I would get it done sooner rather than later. At 2000-3000 RPM a shaft banging around will stress the transmission and perhaps stuffing box. I'd hate to have the trans go out for what amounts to a simple repair. Depends on the amount of "bouncing".
As far as I know, cutlass bearing replacement can not be done it the water, so the boat will have to be hauled and the prop pulled. A good yard will have a hydraulic extractor that does not require pulling the shaft too. Once they have the new bearing in hand and the boat out of the water, the actual replacement should only take about an hour or so.
If you don't have to be somewhere, it may make sense to stop. On the other hand, I expect that you're trying to get out of the way of Hanna. Best of luck!! Be safe.
Sabre 38 "Victoria"