We have the exact same situation("HOPEFULLY" arriving in MCO at 1130pm, hopefully at resort by 230am). At first, we had a room booked at POP because that arrival at at 230am was a "waste" of a night since it was basically the next day so we booked the value to save money (we are then moving to CSR). After thinking about it for a few days, I realized that my room at CSR the next day may not be ready until 3 and I will have to check out of POP and wait for checkin all within a days time. It wasnt worth it to us, so I actually switched POP to CSR so when we check in, at least we have that room guaranteed ready (with a 2am checkin) and the continuation of the stay to consider! I know it kind of stinks but having a room your arrival night is totally worth the peace of mind