Does the loophole still exist that allows someone to book an on-site hotel for part of a trip and book Fastpass reservations after check-out for the remaining part still at the 60-day threshold?
Also, what would happen to Fastpass reservations made at 60 days if the on-site hotel reservation was cancelled? Do you think they’re:
a. retained
b. retained (within 30 days) / cancelled (beyond 30 days)
c. cancelled
The “rolling 60 days” window was closed. You can only make them for the duration of the onsite stay. Also you cannot make them for any days before your onsite stay starts either.
If you cancel more than 30 days ahead, you would most likely lose all FPs.
If you cancel within 30 days, you may lose them, you may be OK.
If it’s a split stay and the second hotel is one of the ones with 60 day privileges and the package you booked with the first stay had more park days beyond checkout, then you can still book them at 60 days. We had a 7 day ticket package with a 5 night stay at CBR, then a 3 night stay at the Swan, and I was able to book FPs for the 2nd day of our Swan stay at the initial 60 day out point. But that was how I realized my kids weren’t on the Swan reservation, since it wouldn’t let me book their FPs past the CBR check out day.
Yes, by onsite I meant the whole duration of all consecutive onsite stays, whether packages or room-only. 
If you have a room-only followed by a package, as before, your window opens up 60 days ahead of stay#1 but you can only book for the period that the tickets are valid for. (There May now be a warning they will be deleted, but that doesn’t happen, because you still have a valid reservation, you’re justbtechnically beyond the 60 day mark).
So in Steenaca’s case, it was allowed because the first on-site reservation was followed by a second.
Does a 1-night stay allow 2 days of Fastpass reservations (check-in and check-out)?
Yes!
Good to know. Thank you both!