Are you thinking about something that is an anti-fouling hard bottom paint, or one which has no anti-fouling properties like the Pettit Racing Bronze? The anti-fouling versions are not completely waterproof. The copper content they contain (which can be as high as 50% of their total weight) slowly dissolves out. In the case of most of the hard paints or vinyl ones, this leaves them somewhat porous as well as eventually ineffective against marine growth. In the case of ablative bottom paints, the whole shebang slowly dissolves away, saving you from the dreadful job of eventually having to remove old hard bottom paint (been there, done that, can still taste that crap, won't do it again). Brightside or similar enamels will not be protected from blistering or peeling from prolonged immersion by painting over them with bottom paint. It's another one of those classic scenarios where the weakest layer of a multi-layered construction represents all the strength you can get out of the entire thing. I've never left a filled canvas boat in the water for days on end, but I suspect filler doesn't have much better resistance to eventual water damage than oil-based paint does.
In terms of resisting water penetration, the closest you can come to completely doing so is epoxy resin with a barrier coat additive, like aluminum flake powder added. This can be home formulated or purchased ready to use. It takes about ten mils of thickness to get serious protection, which can add up to five or six thin rolled-on coats which are then sanded smooth. If you ran your finger down the side of the hull, you could just barely feel the thickness difference where the epoxy layer starts. In this day of high tech stuff, the aluminum flake powder barrier coat additive is kind of refreshingly simple. Any moisture which might try to work its way through the epoxy will also have to zig-zag around the tiny aluminum flakes.