Resales are not much more of a hassle than going through Disney. And once the resale is closed you ar treated just like any other
DVC member. The Timeshare Store, dvc-resales.com, and A Timeshare, atimeshare.com, are the two most mentioned resale brokers on this board and the mentions of them on the board have been generally favorable. (Have dealt with both and had no problem).
With Disney ,you pay the price offered with any current incentives and Disney refuses to negotiate otherwise. Disney's price includes closing costs (about $450 to $500 regardless of how many points you purchase); with resales the buyer pays closing costs unless negotiated otherwise. Also, Disney usually has favorable loan rates (higher than home equity and regular home rates but lower than typical timeshare rates).
You should buy at the resort you plan to stay most because the 11 month ressie window at home resort versus 7 months at others makes a difference--it can be difficult at many times of year to get what you want at 7 months out but easy when doing it 10 to 11 months out at home resort.
If you want OKW, BWV, or now VWL as a new purchaser, you need to go resale because Disney has sold out. BCV, HH, and VB are still avaialble throough Disney.
Resale is definitely something to consider if you are going to pay cash. Price is negotiable. If you have to finance then you need to do a bit of math to make sure your price is fair. For example, if you need to take a loan for a resale that is three points above what Disney is offering on loans, then paying $62 a point may not actually be cheaper than paying Disney $70 (with the current $5 incentive off the regular $75 price per point) because your higher loan rate makes the total payments higher than what you would pay through Disney.