I replaced the winches on my 34 with Andersen 2 Speed 50ST Full Stainless Self-Tailing Winches two years ago. It did require filling the holes and redrilling. As this was part of a deck repaint with all hardware off, I ground out fiberglass in a taper around each hole, filled the hole in the plywood with thickened epoxy and layed in new glass and epoxy on top to make a strong repair. Finally sand and fill as required to smooth out the top before repainting and then drilling installing the new winches.
The Anderson 50ST size is very nice and fits the boat well. If I was to do it again, I would probably go with Lewmar instead (not sure which size is equivalent but you could look that up) - I thought that the Anderson all stainless design would be nice, but the lines actually don't release very smoothly under load if you want to ease a sheet. It tends to stick and then release suddenly. The high end Lewmar winches are likely worth the price difference for smoother operation. Nathan ~~~ Nathan Post S/V Wisper C&C 34 CB Lynn, MA