I recently helped a friend rent points from two different owners for stays at OKW with family for Thanksgiving. I own at SSR but I wasn't renting so I helped him through the rent/trade board.
I would suggest you rent from an owner who has been a long time poster and request confirmation that they own the contract and have the points available to rent. Most owners will have a standard contract to protect both sides.
Most will require a deposit, followed by full payment enough in advance to allow for cancellation w/o point penalty if not paid. You can certainly get the dining plan, but the owner must make the arrangements with Member Services for you.
You will find that the majority of the time, these transactions go smoothly. But remember that they take a certain amount of trust on both sides to make them successful.
Good luck.
