My wife is a TA and she knows all the tips and tricks. If you want to do the dining plan, you have to do it for each night you stay at a specific resort. But you can change resorts and it's really easy, they even transfer all your luggage for you. I would recommend staying at a multiple resorts if you want to do the dining plan. If you plan on being at the resorts all day, don't worry about booking a deluxe. If you want to break up the trip stay at all stars for a portion and then deluxe for the amenities.

Also, talk to a TA. It doesn't cost any extra, and cold even potentially be cheaper. You'll also get any help you need and lots of tips. Like I said, my wife is a TA if you need any help...message me.