Let's assume the worst case scenario...boat still leaks so it wasn't the bellows, transom is shot, coupler is **** because engine is sinking. Atleast 5k in repairs probably wouldn't do. Wouldn't sell to someone with out disclosing it is a major project boat...what do I do with it? Take it to a dump?
That's really hard for me to answer. I bought a decent 25 year old boat. Means I ended up spending a few thousand fixing the crap the previous owner did a great job covering over for me. Biggest thing was, the hull was in good shape and the upholstery was nice. I really don't want to do upholstery work, not in my wheelhouse. After doing the work on it, and figuring out a lot of the drive repairs, I bought a rotted out hull with a bigger motor and newer outdrive. I was going to either fix it up and sell it or pull the parts and put in another boat with a bad motor. Neither happened, I pulled everything and installed in my older hull. Hard to believe, but I broke even parting out EVERYTHING I pulled and everything I didn't use from the junker. Motor, drive, trailer, pump, seats, etc, you name it, I sold it on CL. Paid for my upgrade to a V6.
All that said, I am not running around looking for another junker. It's a crap shoot and it's a lot of work. But I enjoyed the hell out of the build. And I know every fiber and every screw in every part of my boat from prop to bow.
You can obviously figure out how to sell off or part out either the complete boat or its components. And it might very well be fixable with some TLC. Ya gotta want to do the work. And nasty work it is. If you tackle a transom, take it from me - the damage is more area than you at first believe, and it pays off BIG time to remove everything from the back of the boat while you do it. Clear it out down to bare glass before doing any work. You'll be taking it all out by the time you're done anyhow, I kept taking it out piecemeal and that was my biggest mistake. Get it all out and in boxes.
Cost - I didn't spend much over $500 doing the transom myself. I own almost all the tools though. I did buy a couple, like an oscillating saw. So maybe $700. I had fun doing it, too. And it is RIGHT. My boat is smaller than yours though. And I was able to piece in the center half of the transom. Wouldn't have taken that much more to do the entire thing - if I'd cleared everything out first instead of the silly me taking it a little every day.
Rick