There's very little situation where it's workable. As noted, all must go through ROFR. Effectively it's simply 2 separate sales transaction that happen to be linked. And it really doesn't help either party out unless you can hook up directly and avoid sales commissions. I've traded another timeshare for a DVC package and had several trades in the works for one DVC for another. Ultimately one party ends up either trying to take advantage of the other or at least over values their situation compared to the other. Ultimately it's usually better just to add on and possibly rent any extra points than sell to rebuy. The exceptions are when downsizing significantly either in terms of resort cost or number of points.