UpGrady has it pretty much covered I think. I have just a few additional comments regarding my experience with my particular boat. My transom needed to be replaced when I repowered, my problem was not the drives but the underwater cockpit drains. On my boat the drive cutouts were sealed well and had not leaked but the holes in the transom for the cockpit drains were not glassed over after drilling. The rot in my transom had migrated from the drains. If you do tackle one of these boats I would pull all the drains and fittings and check them. Like UpGrady I have renewed lots of hoses, thru hulls, fuel lines, cabin windows etc. In my travels around the boat NONE of the holes drilled for these fittings had been sealed. Well the cabin windows had been sealed and the fittings themselves were sealed to the hull but none of the drilled holes had been. Even the holes for the fuel fill and vent lines going through stringers and such did not have any resin to seal the wood and glass. In the past few years I have been removing fittings and sealing. One fitting I was particularly concerned with as the boat got older was the drain for the fish box/storage area between the helm seats. The thru hull for this drain is located at the water line on the stb. side. The original fitting was nylon and I replaced with bronze. When I removed the original fitting I found that it was cracked about half way around on the inside of the hull. I also replaced the drain hose, it is hard to get to but doable. The hoses I have replaced have shown their age but I don't feel that any were about to fail. I am glad I have attended to them though. I to have rebuilt cabin windows and had the frames for the forward cabin window frames powdercoated as an experiment to see how they would look and hold up. Three seasons in they look like new. I also replaced the plexy with a darker tint while they were out.
So I guess most of it is old boat common sense and you have been through it with your Tournament. The unsealed holes I found were unexpected. Perhaps my hull went trough the rigging area on a Monday.