We rented before we bought in. Just read the listing here about what to look for. It is solid.
Depending on how the owner handles it, it can take a little trust on both sides. The person we rented from sent us a basic contract, we signed it, they booked the res and sent us the number immediately. I checked it to make sure it was legit. Then we sent him a personal check for some percentage (i dont remember the exact split) and we had to pay the rest by 90 days out. In that case, the owner is making the rez without payment trusting that Id pay. Then I pay trusting that the rez will stay intact. Then he waits until 90 days out (which would have ended up being just outside his required banking window) and trusts that Im going to make good on the final payment. Then I make the final payment and trust that the rez will be there. (I kept checking along the way for peace of mind)
I was very happy with my experience. It was smooth and he was good about making the process simple and easy to understand.
If you follow the guidelines you should be fine. If anything doesnt pass the sniff test of those guidelines dont do it.