I'm not him, but I can answer...
Always make a note of your requests on your reservations. Central Reservations just got a new reservation system that will link up much better with our new property management system that will be debuting sometime later this year. Gone will be the days of having to call or fax 5 days out.
When checking in, the earlier you check in, the better the selection of rooms that will be open to choose from. However, keep in mind, most of those rooms will not be available until later, as they could possibly still have people who haven't checked out yet.
Bottom line though... requests are just that... requests... and they cannot always be granted. Best bet is to prioritize, and figure out what you really want, and what you could do without.