I revisited this idea this morning after popping in every 6 months or so.

My wife and I seem like the perfect target for this - both of us now working remote, and pre-children. I so much wanted to pull the trigger. But after spending 30 minutes on the site this morning, I came away with a no. Here are my reasons:

• As I’m sure has been pointed out here, they push the high value rentals out in time. So if you use your pass to book a rental that starts in 3 months, you are really paying $7,500 for it for the 3 months of $2,500 payments with the inability to use your pass.
• Compared to prior times I’ve looked, stays seem extremely short. I looked for the entire month of January, and didn’t see any stays over 3-4 days. I used to see stays for 12-15 days (I think).
• Combining the duration of stays with the “back to back” rule of 7 days, it would be really hard to get value out of this. If I were to maximize this, I would start today (day 1) and would be allowed to book something 2 days away (day 3). Let’s say I could find four nights. So I could stay day 3 - day 7. I would not be allowed to check-in again until day 14. Then I could stay day 14-18, and then would be locked out until the 25th. Check in 25-29, then locked out for the remaining two days of the month. So in this “maximum use” scenario, I am prepaying $2,500 for 12 nights. And these appear to be very mediocre hotel rooms, not the flashy houses that must be booked months ahead.

I’d love to be talked into this, but from the actual inventory available I just don’t see a great value here