I suggest you take a look at the room videos on
youtube. Virtually every resort and type of room is represented there. Then, knowing what size room you need for your trips, figure out what your top 3 or 4 resorts are. On your next trip, take a walk around those resorts. If you ask nicely at the front desk, you may find that they can "slip you in" to see an actual room (but don't expect this to always be the case, especially if you want to see grand villas, bungalows, or cabins). The best advice I can give is, once you have decided on 1 or 2 possible resorts, rent a night or two there and see how it works for you. The cost of renting for one or two nights is a pittance compared to the cost of
DVC, and will sometimes change your mind about a resort.
When my wife and I were looking, we considered 3 resorts. One we were very familiar with, because we had stayed there at least 10 times in regular hotel rooms. We crossed that one off because the DVC side was on the side of the resort we didn't like. Of the other two, we thought the one near Epcot was the stronger contender until we rented there. We HATED the views from both sides of the hotel. Our third choice, BLT, was a surprise winner. When we walked into the lake view room (on the 12th floor, looking at the marina), we knew this is where we wanted to stay. We then began an almost year-long process of watching for "just the right resale contract" (right use year, right size, right price). I finally found that Cinderella contract, immediately put in an offer, and bought it. Since then, we've added on twice at the same resort so we could extend our vacations. We just returned from a 12 day stay yesterday, and my wife is already planning next year's 14 day stay.