We purchased thru Disney directly in 1993 and the price was $56. We purchased our first resale a couple of years later at $54 per point. We have a total of 4 resales ranging from $50 to $60 - the last was in 1999. Some of those had no closing costs (paid by the seller) and some we paid all closing costs.
The pricing has not really been set by the resale brokers, but has been "strongly influenced" by the ROFR floor set by Disney. IMO, as long as
DVC continues to purchase resales below a certain (unpublished) level, ROFR will be a factor in resale prices ... and as long as DVC is still building and selling new resorts and raising the selling price for those, resale prices will also rise accordingly - again dependent on ROFR.
In the past, resale prices have followed the price increases for the new resorts - usually lagging by only a short while.
As for resale pricing in a few years - that is a very speculative topic. As long as DVC is still raising prices, exercising ROFR and extending the expiration date, I expect to see resale prices continue to follow suit. At some point in time, any resorts with the 2042 expiration will likely see a drop in resale pricing (providing DVC stops it's ROFR for those resorts). If the other resorts are also extended, as was OKW last fall, I would expect to see prices rise indefinitely.