Great idea checking the following night's availability before asking for late checkout ^ . That is a huge factor in the front desk decision to give you the time you need. In my experience, being Diamond at Hilton gets me 2pm, no problem about 80% of the time, although I rarely ask for/receive later than 3pm. As a Silver with Marriott, I bat about about 50% with getting my preferred 2pm time.

Always start at 3pm, and it makes the desk seem like we are compromising....I agree, never START with the time you really desire .

The other factor involved is the size/brand of hotel. Your typical CY, FI or RI has limited housekeeping abilities. Also, in the case of a suite/full kitchen brand, more details to freshen and clean. If a hotel has housekeeping staff 24/7 it should be a no brainer to get a mid afternoon checkout (ie a Renaissance or Marriott). If sometimes I get flak, I will jokingly mention that there were housekeepers on my floor when I checked in or were doing turn down service.

Again, from my glorious front desk Hampton Inn days, our owner wanted housekeepers GONE ASAP, so we were never to give later than 1pm, even if you were 5X Diamond . If we were slow, and you had a room type that was popular, I could go to 2pm....again if I was certain we could just leave the room unrented and just clean it the following day. Believe me, that was rare, but I tried....(popular = many in room inventory)....

6PM checkouts to Everyone!!