Just returned from a weeklong trip at CBB. In addition to 2 paid nights of OWB + pool, We had 4 nights booked on points + free night certificates and received upgrades to OWB + pool on 3/4 of those, so 5 of the 6 nights OWB overall. Ask for the host Daven - I am not 100% sure that he had the authority to actually upgrade us, but he was extremely helpful and was the one who told us we received an upgrade when we got off the transfer boat, so it certainly wouldn't hurt to ask. Diamond member here.