For what its worth, my documentation hadn't worked its way through the system when it was time to take the new boat on a trip to the Bahamas. With my purchase paperwork and copies of my application for USCG documentation, I cleared into Bahamas and then back into the U.S. and nobody batted an eye.
There are enough real problems in life that may need my attention that I try to not sweat the small stuff.
We took a boat with expired U.S. Documentation to the Bahamas several years ago, and didn't even notice until we were pulling out the documentation paperwork to clear in.
We just handed it to the Bahamian officials without saying anything and they cleared us in without even mentioning it. However, later in the trip, we got boarded by the U.S. Coast Guard, in the Bahamas, and they did write us up for it. But, we didn't have to leave the Bahamas.
And, I guess the statue of limitations have passed, so I can say we just came back to the U.S. without clearing in to avoid getting hassled again. Never heard anything from that, either.