I have only done it once after my flight fiasco. I have cruise friends that do it all the time without any problems. They live in ATL though and have a direct flight. I have only had one close call with a delayed flight from RDU. Fortuneatly, I was flying AA and staying over with my sister, who happened to work for AA at the time. She called them that morning and had us re-ticketed somehow. We were flying to SJU that day, and was already nervous enough because it was only a few weeks after Sept. 11th. We made it just fine, I was sure glad to see the Holiday that day.
I think it will be fine, people do it everyday without any problems. Get the insurance though.