Tales & Trails of a Traveling Wiseguy

Every year around the start of the year I take stock of my balances in various frequent traveler points programs, both to see how we'll I've done in accumulating & using miles as well as to set goals for the coming 12 months. Yesterday I posted a wrap-up of my airline miles and status for 2025. Now it's time for the same with hotel points and status.

This check of points and status comes at an odd moment. I feel I am at a tipping point where it may be time to say "Game over" for the hotel points-and-status chase. Hotels have been watering down the value of elite status. "Room upgrades as available" often are not available. And when they are, the "upgrade" is something close to trivial like the same room on a higher floor or facing the garden instead of the parking lot.

At the same time hotels have been watering down the value of their points. They do this by increasing the amount needed for redemption. Yes, that's been a story most of the 20 years I've been in the points-and-status game, but over the past few years points inflation has gotten out of hand. Hotel rooms routinely now cost 2x the points they could be purchased for just a few years ago.

This runaway inflation puts emphasis on the strategy of earn and burn: earn points (from stays and credit card bonuses) and spend (burn) them quickly, before they lose value. The old strategy, from years ago, of saving up points for years to redeem them for a week-long stay at a top property is broken. Thus as I inventory my points and status I indicate accumulating too many points as a bad thing and managing to spend down my balances as a good thing.

⬇️ Hilton: More Burn than Earn... And I Got Burned!

Hilton edged out Marriott to be my #1 hotel chain again in 2025 (ditto last year, in 2024). I stayed 16 nights with Hilton. The majority, 13 nights, were paid. That's because either (a) they were for work, and the company was paying; or (b) the cash price was reasonable while the points price was through the roof. Unfortunately "through the roof" has become the new normal with Hilton as they have broadly increased their hotel points costs three times in just over a year. 😧

The one stay where I redeemed points was when both the cash price and points price were through the roof. When we visited Rome in May we stayed at the Waldorf Astoria Rome Cavalieri for 3 nights for a whopping 85,000 points per night. (After the latest devaluation it's 120,000 points per night.) I try to make Hilton points worth at least a half cent apiece, so that's $425 at par. But hotels were eye-wateringly expensive across the city at that time. Many were $600+, including the Cavalieri. So while it was a lot of points it was at least a good value.

Status-wise I regained Diamond (top tier) elite after dropping to Silver (bottom tier) at the start of the year. Diamond is a benefit of the Hilton Aspire American Express card I signed up for again in April. I say again because I canceled it in 2024 thinking I'd find some kind of sign-up bonus for it again. Alas I did not. Is the card with its newly raised $550(!) annual fee worth it without a big signup bonus? My plan is for the answer to be Yes; I'll check back on that after the card's anniversary in April.

Thanks to spending 255k points on that Rome Cavalieri stay I spent more Hilton points than I earned in 2025. My balance dropped from 477k a year ago to 385k today. My goal with the remaining balance is to find an enjoyable luxurious stay for 4-5 days. I need to do it ASAP before Hilton hits us with yet another deval It'll have to be cheaper than the Rome Cavalieri, though!

⬇️ Marriott: Bonvoy-age, Marriott!

Marriott was my #2 hotel chain again 2025, falling just behind Hilton with 15 nights (16 if I include one Hawk did on her account). Back in the 2010s Marriott was my #1 choice. I routinely hit 50+ BIB (butt-in-bed) nights a year with them. My overall amount of travel, especially business travel, has decreased since then. And Marriott has gotten... unfriendly. Their prices in many markets are 15-20% higher than their competition, and getting elite benefits from them is like pulling teeth. Benefits shouldn't be hard; I'm a Lifetime Titanium elite! But here we are.

You may have seen a news stories recently about a Marriott that shooed customers off a bench and a Fairfield Inn that posted that bottles of water are no longer an elite benefit! When they nickel-and-dime loyal travelers that hard getting a real benefit like a suite upgrade seems to have a snowball's chance in hell.

In 2025 I succeeded in spending down my Marriott points balance. It's a goal I'd been working on for years. Why was it so hard? It was hard because I insisted on getting good value for my points. The thing about airline/hotel points nowadays is that while you pretty much always can use them for any trip, you're frequently charged a terrible redemption rate. I spent my balance down from 160k last year to almost zero this year. With earnings from a few paid stays I made, I finished the year just 32k left.

For 2026 my plan for Marriott is, basically, "Bonvoy-age!" I'm done. I'm out. I'll be content to stay at Marriott and use my elite benefits if work sends me to a Marriott, or if I happen to find a Marriott at a competitive price (unlikely!) when traveling for leisure, but I am absolutely not going to go out of my way to choose them. Those 32k points? Meh. Once upon a time they would've bought a night at a resort high rise in Hawaii. Today they might— might!— be enough for a one-night stay at a Fairfield Inn along a highway. And I'll have to pack my own damn water bottles.

⬆️ IHG: Burn and Earn

Intercontinental Hotels Group (IHG), whose portfolio includes Holiday Inn and Holiday Inn Express, remained  my #3 hotel chain in 2025. I stayed 8 nights with them... though that increases to 12 if I count in the nights Hawk and I stayed with IHG on her account. (She's burning off points, too!) Every year recently it's looked like IHG will leap ahead of the others, as its footprint of plenty of decent limited-service properties in smaller towns than Hilton and Marriott fits our travel patterns well. But this year even their prices were just too high much of the time.

My goal with IHG for 2025 was to burn down my points balance of 212k. Hawk had a similar goal, too, as she had about as many points as I did! Plus we both have free-night certificates from the IHG credit cards we own. How did we do? We both spent our balances down somewhat. We used the certs first because they expire after 12 months, and we both redeemed some points, too. But then I signed up for another IHG credit card midyear, and earned 140k from the juicy signup bonus. I finished the year more than 100k above where I started, with 316k points.

Status-wise I remain Platinum with IHG, a benefit of owning their affiliated credit cards. Platinum is their second highest tier. In the past I've groused it's not worth much because there really aren't elite benefits to be had at the limited-service properties I make most of my stays at. Usually it's an "upgrade" to a "suite" at a Holiday Inn Express, where it's just a slightly larger than basic room. I mean, I appreciate it, but to me it's not worth more than maybe $10 a night.

For 2026 my goal with IHG swings back to Burn, baby, burn! 316k points is not the huge balance it may seem at today's devalued rates, but I'm going to see if I can redeem it for a 4-5 night stay someplace nice this year.

↔️ Best Western: What do I do with these points?

For several years Best Western was been down in my "Whatever" category (see below), the group of hotel chains I stay at so infrequently I just don't care. For example, I didn't touch BW at all for years. But the chain came back on my radar in 2024 as they do what IHG does at the lower end, but even moreso. And as IHG was too pricey much of the time, I traded down to BW several times in 2024. That left me about 24k points at the end of 2024... which I still have at the end of 2025. Thus my plans for 2026 remain the same: find some reasonable redemption, presumably a one-night stay somewhere not too swank, for my BW points.

↔️ Hyatt, Choice, Wyndham: Whatever

I have memberships in several other hotel rewards programs. Some still have scraps of points left in them from years past. Others are zeroed out due to expiry. I've barely paid attention to these chains for the past few years because the ones above largely meet my needs— and they control a huge portion of the mid-scale and upper mid-scale hotel market. That said, I did stay for 2 nights at a Hyatt (my employer's choice) and 1 night at a Choice (my choice). Plus we stayed 5 nights with Wyndham on Hawk's account. Between those two I was disappointed with Choice and slightly impressed with Wyndham. That reversed my expectations as previous I'd ranked Choice ahead of Wyndham. We should figure out if Hawk has enough Wyndham points yet to be worth anything, like my BW points (above) are worth potentially a few night somewhere.

I think my future will involve a lot more stays at these other brands as I see declining value in elite status and accumulating points, and instead pick whatever property offers the best quality/price tradeoff in the moment.

The mileage run I flew on Southwest Airlines this past weekend cinched my renewal of A-List Preferred ("A+") status. I saw that reflected in my account within 90 minutes of completing the flight—Southwest's long maligned IT seems to be improving, quietly— and today I got a "Welcome back" email.



Of course, it's not really welcome back... I never left! I've been A+ for all but a few months out of the past dozen-plus years. Maybe Southwest's long-maligned IT isn't so spiff now, after all. 😅

And in the summary of benefits they sent me they left off the absolute most-important (to me) A+ benefit: the ability to select extra-legroom seats at time of booking, for free.

So, was it worth it? Are the value of these A+ benefits worth the time and cost of the mileage run?

The MR had a hard cost of about $110 (cash out of pocket) plus soft costs of 9,000 mileage points (which have a substitution value ranging from $100-200) and several hours of my time. The value of these is not trivial. As for the value of A+ status next year... Frankly, I'm not sure.

What the A+ status is worth over the coming year depends on how much I end up traveling— with job and life changes expected that's hard to predict— and how Southwest's policies shake out. They're changing their whole customer-facing business model right now, doing away with open seating and free bags. Their austere new rules are sure to fuel a lot of customer outrage. If that translates into plummeting demand they may have to revert some of the policies. It remains to been seen how it all lands.

One thing I can tell you 💯 is that flying a mileage run was NOT my first choice! There are so many ways I would've preferred to renew A+. The MR was, like, my fifth choice.

• First choice, my original plan, was to re-up A+ with a bonus from credit card spending. But then I realized 3 weeks ago that I had miscalculated the spending for the credit card bonus. The pisser is I was short just a few hundred bucks. I could've put that extra spend on the card easily, and at no cost to me; but by the time I caught the mistake it was too late.


• Second choice was to have even one more business trip late in the year. I tried. Customers just dont' want to meet face-to-face anymore.


• Third choice was to manufacture a leisure trip— to go somewhere and enjoy being there. My partner's health problems put the kibosh on that.


• Fourth choice was to just buy status, without having to fly. Indeed, Southwest came through with a status-buying offer a week ago... but it was hideously bad. 😡

Next year I'll almost certainly be working on a plan like #1 again, earning A+ —if I choose to keep chasing status—with a the help of a credit card boost. While I'm already keeping careful track of spending for that bonus I'm not going to try to over-optimize it again like I did this year. I'll spend at least a few hundred over the threshold just to cover myself in case there's a discrepancy between my calculations and Southwest's. Because while this MR ended up being not too difficult and gave me a funny story to tell— being in Los Angeles just long enough to piss— I would've preferred notching the status without the expense and uncertainty.

Flying for Fun & Profit #1
SJC Airport. Sun, 28 Dec 2026, 3:30pm.

This afternoon I am embarking on a mileage run. It's a flight taken strictly for earning points snd status. A few weeks ago I saw I was coming up a tiny bit short on my Southwest status chase, so I booked this mileage run.

For this mileage run I booked a quick round-trip to LAX. But I'm not going to Los Angeles, other than spending a few hours on the ground at the airport. I get back on a flight home this evening.

Right now I'm at SJC airport. I arrived here well early for the first flight. I'm taking as few chances as possible with the schedule.

I've been checking the flights for on-time-ness all afternoon. The aircraft for my first flight has been tracking on time and just landed from its previous leg. The homebound flight has been drifting a bit late, probably picking up delays from coming from somewhere in the East, where snow has caused lots of cancellations. That flight being late is okay... I'd only get worried if my outbound were late, because then I might miss the homebound! I planned over 3 hours on the ground between flights, so the chances of that are small... though never zero.

Stay tuned, this should only take a few hours!

Update: the flight to LA was smooth, then I took a piss and I turned myself around... that's what it's al about!

One of the benefits to Costco Executive Member status Costco rolled out earlier this year is letting Executive members start shopping an hour early. When I wrote about whether Executive membership has been worth it (spoiler: arguably it isn't) a few days ago I mentioned that I've thought several times about hitting up Costco early in the morning for Executive Hour but never actually did it. I always figured, "Nah, I'll just take it easy at home this morning and brave the madding crowds of the hoi polloi later in the day." 🤣 Well, today I finally shopped Executive Hour.



I was up early anyway today because I had an early work meeting on my day off. That's right— not only did I work on my first true day of vacation but it was an early morning meeting! After that I went out to the clinic for a blood draw, then when I came home I had a quick breakfast while Hawk jumped in the car with me to go shopping. At Costco.

We arrived at the Mountain View Costco around 9:15am. Normal opening hour on weekdays is 10am. For Executive members like us, the store's open at 9. And as we pulled into the parking lot, hoping to find a nice, close parking space instead of the usual automotive mob scene, we found... the parking lot mobbed just as much as 1pm on a Saturday.

"Wow, everyone in Mountain View must be an Executive member," I quipped. "And when everyone is Executive—"

"—Nobody is Executive," Hawk finished the line for me. 🤣

So, yeah, that Executive member perk is close to worthless, at least here in the Bay Area.

I've remarked a number of times that airline elite status is important enough to me, given how much I travel, that I track my earnings on a spreadsheet. I've got lifetime gold status on United so I don't track that anymore, but I do track my Southwest earnings rigorously. All this year I've been watching my elite qualifying points and forecasting my future flight and credit card activity to map how I can get the 70,000 points to renew A-List Preferred (A+) status.

Back in October it seemed like it would be a long shot to get A+. A long shot but still doable. Then a better plan came together in November with a business trip to Austin. I saw a clear path to cinch A+ by now. When the final points I needed failed to post recently I went back and checked my records. It turns out one of my estimations was off. I am currently 140 points shy of the 70k needed. A lousy 140 points out of 70,000!

So, how can I earn points to make up the difference? This late in the year there's only one way: fly. Fly on a paid ticket. Thus for the first time in 14 years I am going on a Mileage Run.


I scoured Southwest's booking engine yesterday and came up with cheapest trip I could find. December 28th I'll fly a completely gratuitous round-trip to Los Angeles (LAX). I'll fly down in the afternoon, spend a few hours on the ground without even leaving the terminal, then fly back late evening.

What's it going to cost? The one-way flight that gets me the points I need is $109. The other flight I bought with points, 9k.

Is it worth it? Hard to say. A lot of depends on what A+ status is really worth next year. It's kind of a big question mark because Southwest is completely revamping its customer operations with assigned seating. Nobody really knows what it's going to look like in terms of getting good seats with the new policy. But A+ elite status gives me the best crack at it— and like I said above, I fly enough that it matters. So I'm spending some money now to buy a better experience across all of next year.

Yesterday my boss suggested a plan to help me reach elite status. At first I thought he might be joking because he brought it up in a laughing manner, but as he explained it there's a real there there.

His idea was that our AE (account executive) counterparts often seek to "protect" us from having to travel as we head into the end of the year. Except those of us who do travel as part of our jobs are concerned about reaching elite status. And as we head toward the end of the year we're keeping an eye on how many more miles/points/trips we need to qualify. He talked about getting his team together to discuss how much more each person needed for the year then telling the AEs, "Hey, you need someone to help you cover a meeting? Reach out to Chris, he needs 4 more trips this year for elite status!"

"I need just 1 more trip, possibly 2 if it's a short/cheap one," I said right away. I needed no delay to think about it because I've already been tracking it. I explained to my boss how I created a spreadsheet years ago, modeling it kind of like a sales forecast, to track progress toward elite status.

I also told him about how hardcore frequent flyers do Mileage Runs (MRs)— trips they take purely to earn status. I did an MR, just once, years ago.

I gently pushed back, though, on the idea of telling AEs to help book work trips for us. I did that because I don't want to create or perpetuate a notion that we're arranging business trips for personal benefit. I do push for meeting customers and prospects face-to-face, by traveling to visit them, instead of meeting via videoconference. I do that because it makes business sense, because it's more valuable for the company, not because it's a boondoggle or for status bragging rights.

Phoenix Getaway travelog #12
Now at PHX airport · Tue, 23 Sep 2025. 1:30pm

We're at the airport now, chilling before our flight home in 2 hours, but before coming here we did enjoy a last hurrah at the resort this morning.

We got up early this morning, around my usual weekday 6:45am alarm. Aren't we supposed to sleep in on vacation? Well, yes and no. When the sun's up early and sets early it makes sense to make good use of daylight. And it's not like we were up late last night anyway. We tried using the resort's hot tubs after dinner but both were broken. One had no heat, the other had no jets. So after a short soak we returned to our room for the evening.

Breakfast at the Cafe

Since we were up early today we opted to sit for breakfast in the hotel's small restaurant. The past few days we've contented ourselves with eating protein bars in the room so today we decided to splurge a bit. Plus, one of my elite benefits here at the Hilton hotel is a $30/day food credit. Yesterday we used the credit toward our lunch at the pool cafe. Today we figured we wouldn't stay late enough for lunch so we used it toward breakfast. Not that it covers breakfast. $15 each doesn't even get the job halfway done when breakfast plates are around $20 apiece, plus $5 for a juice or soda, plus tax and tip. But it changes the cost calculus enough that we enjoyed dining out instead of eating protein bars in the room.

Quiet Morning in the Water Park

After breakfast we returned to the room, relaxed a bit, and changed into our swimsuits to hit the lazy river just after its 9am opening time.



Yesterday was pretty quiet at the water park. Today seemed even quieter. Even though this is a great time of year for #PoolLife in Phoenix— the weather is hot but not too hot— the resort hasn't been too busy. I figure that's because school's back in session, so families aren't taking trips outside of the weekend. And even on the weekends they're buying fewer day-passes as kids are busy with sports and other activities on the weekends. And that was all part of my plan for why to make this trip now. We balance great summer-y weather— even though today's high of 100° is crisp Fall weather by Phoenix standards 🤣— with less crowding.

We spent a few hours at the river ranch this morning, alternating between floating around the lazy river and relaxing on lounge chairs in the shade. Come 11:30 or so we decided to call it a day... er, morning... and headed back to our room. I'd arranged a late checkout of 1pm so we could shower, change, and pack our bags after using the pool.

Making Time to Shower and Change

The late checkout wasn't strictly necessary. The hotel is fine with guests staying in the water park all day after the normal 11am checkout. We've taken advantage of that policy several times in the past... packing our bags in the morning, stowing them in the car, staying in the pool area until sometime mid-afternoon, and changing in one of the bathrooms when it's time to leave for the airport. But having a room to go back to is more civilized, and today the timing made sense for that. Plus, taking a shower in our private room instead of changing quickly in a public bathroom has made me feel a lot more refreshed.

Little Charge for Charging

Like I said at the top, we're chilling at the airport now. Oh, returning out rental car involved a bit of... weirdness. Remember I maligned renting an EV because figuring out charging without an annual subscription is a pain in the ass. And expensive. Well, I decided to simplify the conundrum of "a pain in the ass and expensive" down to just expensive and return the car with 60% charge to the rental depot and pay whatever ridiculous marked-up rate they charge for electrons. Y'know, like how they charge you $6/gallon for gas if you return the car less than full.

I noted the less-than-full battery to the attendant processing car returns and asked about the cost.

"It's only 12 cents," he said with a chuckle. "We'll email you a receipt."

"12 cents per kilowatt hour," I responded, "That's great. Without a membership the commercial recharging stations are charging 48 cents on up."

Except I'd misunderstood him. The rate wasn't 12 cents per kilowatt hour— which I estimate would've come out to $4 or $5 total to top off the battery. I checked the emailed receipt just now on my computer, and it shows 12 cents, total, for the electro-fillup. Bonus!

L.A. Trade Show journal #3
Downtown · Tue, 16 Sep 2025. 9:30pm

I'm at my hotel in downtown Los Angeles. It's the Moxy hotel, in one of the newer high-rises downtown. Actually a lot of the high-rises downtown are new to me. The last time I stayed in downtown LA was in the early 00s, and there's been a building boom since then with new hotels and residential towers.

I knew when I booked the Moxy that the rooms here are small. Like, tiny by US standards; and more like what I saw at salaryman hotels in Tokyo. But still I didn't expect it to be quite this small....



I have to squeeze past the foot of the bed to get to the other side. The only furniture in here is two tiny nightstands and a kid-sized chair. One of the nightstands is meant to double as a desk— and that's what the tiny chair is for.

Also, the gal at the front desk who checked me in gushed about my elite status (Marriott Titanium) and the upgrade they had for me. It's an upgrade to a City View room. Except the city view is a view of the convention center, two major freeways, and a freeway interchange.

One big plus, though— and this is the primary reason I booked at the Moxy— is that the convention center is right across the street. I won't have a long trek tomorrow to/from the show, which will especially be good if I need to make the trip twice.

Update: The longer I spend in this room the worse its design gets. It's like the designers didn't even spend 2 hours trying to stay in this room, even as a solo traveler, for even a few hours, let alone a full night. In addition to the problems I identified above, there's pretty much no horizontal surface onto which to place things. Need to lay out clothes to change into? Lay them on the bed. Need to open a briefcase to find something? Have to lay it on the bed. I do not like using my bed as a workbench, but here I have to! Hanging clothes is silly. The only places for hangers either (a) leave my clothes dragging on the ground because they're so low, or (b) have my clothes hanging over the front of the TV because, yes, that's where the hanger hooks are. And the lighting in this room is terrible. It's like living in a dive bar.

Next up: A Day at the Show.

Canada travelog #29
Maple Leaf Lounge, YYZ Terminal 1 · Fri, 29 Aug 2025. 2:30pm.

Getting through the airport shuffle at YYZ today was... well, I won't say swift, because par for the course at YYZ it felt like we had to walk to Mississauga and back, but it was at least uneventful. There weren't really any lines....



Passport control had more agents than travelers. I've read that trips from Canada to the US are way down thanks to our bellicose president. I wonder if the lack of crowding here at the passport queue is due to Canadians choosing not to travel to the US, or just due to the time of day. I'm certain it'll be more crowded late Friday afternoon, but how crowded?

It was also quiet here at the lounge when we arrived just after 2pm. Access to partner lounges is one of the benefits I get from my United Airlines Gold status, and Air Canada is a Star Alliance partner. If there were a United Club lounge here I would not get in for free, because United does not consider Canada "international" for purposes of its international travel benefits. (United was waaaay out ahead of President Trump, years ahead, in verbally treating Canada as "the 51st state".)



Hawk and I are sitting down now, enjoying a meal in the lounge. They've got a little buffet going that today has bulgogi, pesto pasta, and sauteed broccoli. It's an odd combination, but it works. And it's free and it's tasty.

Speaking of combinations, my beer in the photo is a combination. The lounge has a few beers on tap, including Smithwick's Red and Guinness Stout. I poured myself a Blacksmith.

Update: By the time I left the lounge around 6pm I'd eaten another plate of food and knocked down a Manhattan and 3 Gin + Tonics. 🥃🍸😋

Canada travelog #31
Back home · Fri, 29 Aug 2025. 11:20pm.

We are back home from Canada. Our flight, a nonstop from YYZ (Toronto), landed at SFO around 9:40pm. We had bags in hand just after 10, were rolling in a car by 10:15, and walked through our own front door at 10:45. Now it's 11:20pm, I've unpacked, I've taken a shower to clean the travel stink off me (it always smells like old-lady perfume), and I'm winding down before going to bed.

Travel home this evening was mostly unremarkable. Hawk and I enjoyed putting our heels up for several hours at the Air Canada Maple Leaf lounge courtesy of our United Airlines elite status. That was worth a pretty decent free meal along with a comfortable place to sit while we killed about 4 hours at the airport before heading over to our gate to board. Oh, and I killed several drinks, too. Flying 5.5 hours in coach was easier when well lubricated.

...Except I didn't fly in coach. At the last minute, as I was queued up for boarding at the gate, I looked at my electronic boarding pass and saw that my seat assignment was changed to 1E. Cue Bob Uecker: I must be in the front row! 🤣 First class wasn't much of an upgrade from the exit-row aisle seat I already had in coach as it was a domestic aircraft. (Domestic First is nothing like International First.) It was basically just a wider seat and free booze. But: wider seat a free booze! 🥳

The only thing that was a disappointment about today was that we cut our trip short by 2 days. But that's not really a "today" disappointment; it's a decision we made on Tuesday after the dry balls let-down. We called an audible and rebooked our flights to return home 2 days early.

Calling an audible isn't just about cutting trips short, though. It's about swapping out something that's not working as well as planned for something else, a Plan B, that'll work better. So, what's Plan B here? We're not sure. We've still got a three day weekend since Monday is Labor Day. We may pack our bags back up and head out of town tomorrow! Or maybe we'll stay around town, hang with friends, and spend warm, sunny afternoons at the pool. It's like there are no wrong answers here.