Well, there are a few things you need to remember when requesting rooms.
1) Make sure you note your requests on your reservation as soon as possible, and I recommend faxing in your requests again 3-5 days before your arrival.
2) Priortize your requests when you send them in. If the MOST important thing is being close to Classic Hall, note that first, followed by requests for the floor you'll be on, connecting rooms, etc. If you booked 2 rooms and your reservations are "linked", then they'll automatically put the two rooms next to each other. If it's more important to be on the 1st floor, then make sure that's #1, and be sure to state that your requests are in order of priority. Don't forget to be courteous in your request fax (please, thank you, etc). If you sound demanding, and make multiple requests, they may pass over your fax or put it aside for the time being. It shouldn't happen, but honestly, if you're not asking nicely, you deserve to be passed over.
3) If you book with a
Travel Agent, I think it's even more imperative that you double check with the TA that your room reservation is linked if you have more than one room, and also double check with the TA that your requests were forwarded to Disney. Then, on top of that, you should still send in a fax. Every time we've faxed we've gotten our exact requests.
4) Remember that all of the rooms closest to Classic Hall are preferred rooms. If you booked a standard room, you can not be placed in these rooms that are close to Classic Hall unless you do book preferred, so check out the maps of which rooms are preferred and which are standard in post #1. Really, there aren't a whole lot of rooms that meet the criteria of close to Classic Hall, 1st floor, connecting. In fact, there are probably only a handful of non preferred rooms that connect on the 1st floor and are reasonably close to Classic Hall.
5) Keep in mind that depending on your request, it will be harder to get what you ask for. The most often requested things would have to be "closest to Classic Hall" so those rooms are going to fill up quicker. To top that off, if you request connecting rooms, there are only so many rooms that connect (not all rooms have the connecting feature), so if connecting rooms is a priority, it's going to be difficult for them to also get you on the 1st floor, and on top of that get you someplace reasonably close to Classic Hall. The more requests you put in, the harder it is for them to meet them. And if you don't state that your requests are in the order of most important, then they may not know, and try to meet what they think is more important (like connecting rooms, for example).
On our trip last month, they met all our requests. I requested, 50s section, pool side view, 3rd or 4th floor, connecting rooms if possible, in that order. I e-mailed our TA with the requests, and then faxed ahead of time. When we got there, I didn't even mention our requests, they had already put us in those rooms (and we got there somewhat later that night than we had expected, around 7:00).
Hopefully those tips will help! None of those things are "official" tips, but from everything I've read, and everything we've done in the past, those are the things that work best and things to keep in mind.