We bought a small OKW contract in 2005 and have loved it. We love the "small" commitment and it has served us well with banking, borrowing and transferring in points as needed.
My best advise is to use the board sponsor and get on their calling list for small contracts. You have to be prepared to say "YES!" when they call, or they'll move down the list and find a buyer, often within an hour of receiving the small contract for sale. We got on the list and I think it only took about 6 weeks to get the contract we want.
My other major piece of advice is to offer ABOVE what Disney is ROFR'ing. There is no sense going through the headache of the entire process to end up disappointed. The $2-3 more per point you'll pay (so $50-$150 more total for a 50 point contract) is a very, very small price.
As for resorts, I always suggest actually visiting them all. I did this before we bought on a trip, and fell in love with OKW right away. I think it is so individual. But, also remember with a small contract, OKW requires the fewest points, so you get more mileage out of your contract.
Good luck!