If you have the time to call CG and talk to them they will outline what you need to do. and i think it is going to depend on access to those past owners for an easy out.

But I thinking that the only real reason to document would be for a newer high priced boat with a steep mortgage on it ... and that probably would be required by the mortgage company ...

I have documentation, but don't see how it has done anything for me for the last 25 years other than not have to stick numbers on the bow.

And documented boats are supposed to fly the US flag, which I like to do anyway. It doesn't cost anything to keep documented once you are documented.