Most hotels will allow early check in or late checkout (which might be a better bet) depending on occupancy. Late check out may be easier because you are already in the hotel. Early check in is easy during the slow months, but during Jazz Festival may not be the time to be making such requests. The other thing is you roll the dice because you likely will not be told until the day of check in.
Priceline guarantees 3 pm check in. One time Intercontinental did not get me finally checked in until 5 pm on a Priceline booking. I said to them, "what about the 3 pm guarantee?" I got free drinks on the Intercon at their bar for my trouble. I think their computer system went down, causing delays in the processing of checking in guests. You are at the mercy of these kinds of "shit happens" events as well. If it happens to you I doubt Intercon will pay the cancellation fee on the escort. They will give you drink vouchers. Most hotels will do the same thing. You can sit with the escort at the bar and have free drinks if the shit happens.
One other time my check in was delayed and the escort date was delayed. This was at the Hotel Lord Berri. I was told that the cleaning staff had some problem. I think they were just slow, and their slowness became my problem. This was a long time ago, summer 2002. I think it was Labor Day weekend, many students were staying at the hotel and the cleaning staff was likely overwhelmed, although hotels should not have to make excuses if they are prepared.
