The two on-line brokers mentioned above (The Timeshare Store and Atimeshare) are experienced at these kinds of sales and the process is fairly easy; not as easy as Disney but mostly painless and quick. With a resale you can negotiate price, division of dues for the year, and who pays closing costs. Often the deal you are looking for will not be in your use year, but all that means is that you will end up with two different use years and two different member numbers--and then you have to keep track of two contracts and juggle them for a trip (no real problem).
Whether going resale or through Disney depends on a number of factors:
1. If you want OKW then a resale is the way as OKW is sold out through Disney. Through Disney right now you would get VWL, VB or HH.
2. Paying cash is a factor that weighs in favor of resale. If you have to finance then you need to do a number of calculations. Disney's finance rates tend to be a few points lower than market rates for timeshare loans and that difference in rates could mean that your actual overall cost for a resale at say $65 a point is more than going through Disney at $75. If you can finance at a low home loan rate (on your existing home) or through a low rate union or employer program then it is possible to get a rate lower than Disney.
3. Closing costs on a resale are usually in the $400 to $500 range and that amount tends to be fixed regardless of how many points you buy. Disney pays closing costs on new sales. The buyer in a resale does so unless negotiated otherwise. Thus, you need to consider the impact of closing costs on the deal. If what you are looking for is a low point, say 50, add on rather than a 150 points or more, then a resale may not be the way to go for two reasons: (a) low point contracts are seldom available in resale, and (b) if you have to pay those closing costs your actual cost per point may exceed Disney's price. For example, a $67 per point 50 point resale with the added $500 in closing costs works out to a real price of $77 a point.
4. Examine closely what you are going to make an offer on. The true value of a resale partly depends on the actual points currently available. A 150 point contract with all current year's points still available has more value than a 150 point contract where the seller has already used the current year's points. You often find seller's seeking high prices for contracts that require much lower prices because the seller has used up all current year's points and borrowed and used up all of next year's points.