Here some of the questions I answered before I bought last month (through resale and an add on at BLT through Disney):
1. What are my travel plans? Do I want to go every year, every other, etc?
2. Do I plan my vacations at certain times or do I go/want to go at different times?
3. Do I plan more than 7 months in advance?
4. What is my favorite park and will easy access to this park be important?
5. Going through resale can save me upfront costs but am I going to be happy with the resorts available?
6. What are the differences in MF at the different resorts?
7. Does the expiration date of the contract outweigh a more expensive point cost at the beginning?
When I bought last month, I knew that I wanted to be at BLT. Walking back and forth to the MK (which is my favorite resort) was important to me and I have held off buying in to
DVC until BLT became a reality.
However, the point cost for new members was a little high so I bought a small resale contract at VWL (my 2nd favorite resort) and then did a smaller add on at BLT.
Going through resale, especially if you are happy with any of the DVC resorts, can save you some upfront costs. Some of the SSR contracts right now are a great price and expire in 2054.
However, Disney is also offering deals for new members to get in at AKL with only 100 points and have incentives if you have a member referral (matching developer points or a cruise).
Lots to think about. People on this board are wonderful. If you post some of your questions, you will get lots of responses and opinions!
Good luck and happy planning!