Pricing is seasonal but also can be dynamic based on demand and may also be discounted if it isn't booked in a short time window (aka Jaunt). A house in Aspen in January will certainly be more per day than in July, for example (although Aspen is beautiful year round..).

I haven't seen what other posters are stating as pricing but I can relay some examples if there are destinations you have an interest in.

There isn't such a thing as roll over days with Club. You pay annually/3 year/5 year for the membership then just book a la carte. Pass is where you would have "days." There isn't such a thing as roll over here necessarily either, however, you can bank days where you would make a booking far out in advance and then cancel. For example, if I book a house in Hilton Head for 30 days for next February, let the 30 days lapse on Pass then cancel, those 30 days will go in your bank. What this means is you could apply to a future reservation or allow you to have multiple reservations at once.

I haven't booked as little as a few days out, maybe two weeks approximately, but generally a month out. For example, I just booked a house in Los Cabos which is about 60 days out (got a very reasonable redemption rate). Otherwise, we have miles with United that I can book if need be or generally book into economy and most of the time get upgraded as a 1K (or can apply PlusPoints etc). We're also in a unique situation that sometimes Economy is actually preferred due to having a little one and all 3 seats being together. You're right though, that is a possibility where some of the savings on the stay are offset by higher flight pricing it just isn't an issue we've come across yet. All told, between flights and Inspirato Pass we probably spend ~$50k/year.