I'm the OP. Thanks everyone for the great information.

I'm strongly considering subscribing to the PASS. But one thing that bothers me (regarding hotels, not homes) the most and preventing me from jumping in....

Many of the stays are too short. For example, I'm heading to Vancouver in early Sept, and the only inventory I can see are all 2 nights at the Rosewood Georgia (great hotel), but I plan to stay 4 nights. So naturally, I would want to take advantage of my PASS, but that would mean checking out (or extending or changing rooms) after two days. Even if we extend, it's likely that the suite we'd be in has a rack rate of $1.5k per night for two extra nights, so it kind of defeats the purpose of the PASS to have to pay 2 extra nights, because I could probably book a lesser room for 4 nights for less than the cost of the PASS + 2 extra nights in a suite. And I can't think of anything more annoying in breaking up a getaway weekend than having to checkout. And I imagine this will be the case for almost all getaway weekends. You can only partially take advantage of the PASS, and then still have significant out-of-pocket.

I did a similar search for London UK for November (and again Rosewood London showed up, great hotel, stayed there many times) and again it was for 5 nights, instead of the 7 that I'm looking for. Same scenario as above. I'd have to extend a couple nights at ~$2.5k per night.

So I'm thinking two things:
1- When Inspirato negotiates these room rates, the hotels expect that the client will often extend a night or two at full rack rate. It's probably part of the strategy.
2- Inspirato reduces the number of nights available the closer you are to the arrival date... 5 nights if booking 3 months out, 3-4 nights 2 months out, 2 nights 1 month out. This would make sense since they don't want to lose money, they won't leave a 5 night inventory option with just 1 month left, I seriously doubt it. So that means that all "last minute" getaways will typically be 2 or 3 nights max, with no option but to extend.

So bottom line, the true cost comparison for PASS is that you have to factor extended nights, and compare that to booking a "lesser room" without PASS. Granted you may not get the fancy suite, but you are still staying in the same hotel without any of the planning commitments needed with PASS.

Just my thoughts. I would welcome feedback from people actually using PASS.