What your purchase budget is will determine quickly if you can afford it or not. Resale OKW are about $85-90 PP in the 200+ point range or somewhere in the 20K range with closing. You'll pay about $8 PP annually or $1600 every January (or divide by 12 monthly debits). You'll need at least that to do a studio for about 2 weeks a year. Buy more not less. Once you are in a 1 BR, it's all over and you'll be buying another contract so plan on it.
At 11 months prior to your much deserved vacation, you'll make reservations at your HOME resort (say OKW for this lesson). At 7 months you can switch OKW out for another resort that you have enough points to stay at, that is available - this is the key...it is getting near impossible to get much at 7 months. Studios go first. You can't be picky at 7 months. Buy where you want to stay.
UY is becoming more important every year. You can bank and borrow (now limited to 50% of next year's points.) You'll need to read up on UY's, banking and borrowing here on disboards. Lots and lots of reading.
If you decide
DVC isn't for you, you can list your contract, pay a commission and say bye bye. If prices are high, you might break even, if you have it for many years you might turn a profit, if you sell in a downturn, well it might be somewhat of a loss...however, you had the use of the villas when you owned. Paying cash initially and then staying for $80+/- per night feels REALLY AWESOME. It's like flying free on airmiles.
Doing your homework is the only way to feel confident in this purchase. We originally bought in 1996 and love it more than ever, warts and all but it is not for everyone. Good luck!