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Wow, that was one filthy boat!

The crack in the transom is likely due to water intrusion, either via the transom drain through-hulls, the lifting hook holes, or the bolt holes for the engine. The water swells the wood and cracks the gel coat. My 16SL has that, but not as bad as yours. If you're concerned about transom rot you can do what I did: I took out all of the above (removing the engine), then aimed some heaters at the transom for a week or so to force some of the water out. Though my wood was damp it wasn't punky, so I got some new through-hulls and resealed everything, including the crack. If you're really concerned you'd rebuild the transom, but I'm not obsessive enough to want to go through that process. You'll need to remove the plate in front of the engine in the transom well to access the lower engine mounting bolts, and also to check for water; if the plate isn't sealed well water will get in and then into the lower bolts holes. (BTW, good to see the engine mounting position a couple holes up, as most engines were just slammed down on the transom, to the detriment of performance and handling.)

Given how old the boat is it's also a good idea to check sealing on all through-hulls. Mine all needed to be redone, and there was some wet foam around them.

As for the ski pylon mounting, I haven't seen that before, and frankly I don't think the tank cavity cover is designed to take the stress. The factory setup can bee seen on this personal page: http://www.whalercentral.com/infusion...r_id=15621, 4th picture down, where the mountings are either side of the transom and the vertical surface in front of the rear seats.

For water in the fuel, check the gasket on the fuel filler.

To get the tank cavity cover off you have to remove the vertical panel in front of the rear seats.

Finally, on the trailer if you're planning to trailer the boat a lot I'd switch from the rollers to bunks. Rollers are generally a no-no on Whaler hulls and can lead to delamination of the skin/core foam or even cracks. And it's difficult to tell, but if there aren't any there should also be keel rollers.

John K.