I'm sure everybody has a different strategy, and the topic of requests/room assignment is a hot topic here. As mentioned, requests are just that and there is certainly no guarantee you will get them. Obviously, the more requests you make, and the more specific you are, the more likely you are to be disappointed in some way.
Personally, I limit myself to the top two things that I really want for that particular reservation. If my MIL is going with us, I need a ground floor room due to her medical needs. After that, my top preference is non-smoking.
For longer stays, I might want to be a little more discriminating about location, although I think there is a real question whether your requested location means anything at all. If the resort is truly using "room ready," theoretically they won't pay much attention to a location or view request unless you are at BWV where certain views are a different category of room altogether. They'll theoretically just assign you the next room that pops up in the computer. If they have half a dozen rooms available, hopefully they would try to meet your view requests as closely as they can.
