While we can speculate here, you won't really know until you try.
Mamiamjo Which dates are you looking for, how many points? You may be able to do so, but as suggested above, you may need two different owners to rent from.
I guess I'm asking for speculation

. I know I sound like an idiot, but my issues are as follows:
1. I'm not sure when we could go. It may have to be over a peak season time (after Pres day, after Easter) which would be between 160 -200 pts for each 2 br villas. If I can take the students out and miss classes we could go in May for about 130 pts for each villa.
2. I don't want try to rent 2 villas at 11 months out if that's going to tie up reservations for people who KNOW they can get what they want and go.
3. Do
DVC owners ever rent their points at the 11 month mark for their home resort? Even for BCV? Would I need to make the agreements to rent BEFORE the 11 month window opened?
4. I read the discussion about renters in the sticky above and want to be as ethical and above-board as possible.
5. I don't even know if I'm making any sense. (Maybe I need a dunce hat sticky now).
6. I won't be making reservations until March 2008 if we go in February 2009, or April 2008 for March 2009. Or June 2008 for May 2009. Is that right?
7. Please, if at all possible, give me a direction or plan to pursue. I'd rather go through the DIS than ebay. Thanks