It seems to me like, if he were to have tried to do the voyage accompanied by a dedicated support boat, then the Coast Guard probably would have let him do it.

It seems to me like, if he were to have tried to do the voyage accompanied by a dedicated support boat, then the Coast Guard probably would have let him do it. On his first trip, the Coast Guard intercepted him, but eventually let him continue, but then a few days later he had to be rescued. On his second trip, they were much less lenient and forcibly removed him from the bubble. So it sounds to me like the Coast Guard didn’t think he had planned well enough to do what he was trying to do safely, and they were probably right. If he had instead done a series of progressively longer trips accompanied by a support ship ready to rescue him, and then planned to do the trip to Bermuda with a support ship, then he may have been able to convince the Coast Guard to authorize him to do the voyage.