You'd get more replies in the "purchasing
DVC" forum than here, as your question is a perennial favorite there.
DVC works best for people who:
1. can plan more than 7 months out, and preferably can plan 11 months out
2. don't need to finance their DVC purchase
3. want to stay in deluxe hotels
4. understand that "free dining" is not a perk they will ever receive
For my own advice, I would recommend:
1. read the stickies in the purchasing board to understand use year, resale versus direct, and what is actually included versus what is a perk for direct purchasers.
2. decide what type of room you'd like to stay in each year and note the points required for that in the season you want to visit.
3. Figure out what resort you'd prefer to stay at most of all
4. Figure out if you can afford to purchase, and pay maintenance fees, on that number of points at that resort.
5. RENT POINTS FOR A RESERVATION at the desired resort, in the desired room type, and see how it goes.
6. If all goes well for you, then start stalking resale listings or call DVC to make your purchase.
I cannot stress #5 enough. My wife and I narrowed it down to three resorts. We had previously stayed at the Poly, and loved it, but didn't like where the DVC rooms were located. We stayed at BCV, and missed being on the monorail loop. When we stayed at BLT, it was "Welcome Home" for us, so we bought there.