if you're talking about renting out points so you can receive cash in return, i've been thru it twice with no problems.
the first time, it was banked points that we had no plans on using, so we rented them out for cash to a person who used them at the GF.
the second time, it was holding account points that we were trying to rent out. this was a little more tricky because we had to first make a reservation with the points and then rent out the reservation (you can't rent holding acct points directly). the rentee ended up buying the reservation and then changing the resort and dates (for same amt of points). it's more work than in the first situation b/c you have to work with the other party a lot more to secure the reservation they want.
in both cases, the transaction was completed with PayPal, and i could see the pending paypal transaction hit my account while i was on the phone w/ the rentee. although the money hadn't truly settled (not until the $$ goes from paypal account to bank account), i felt very comfortable that i had received pmt (more so than if it was done via 'check in the mail'). also in both cases, the rentee was well known in this forum (given the number of their posts); this greatly added to my comfort level.
the folks at
DVC member services appear to be well acquainted with this renting process, and they easily transferred the points/reservation while I had the other party conferenced in on the same line. also, i think they made me fax them a letter showing the number of points being transferred and the name of the rentee.
i would not hesitate to rent out points again, esp. if it could be done with paypal & the person was well known in the forum.