re: CL 36 "issues"
being boatstruck is euphoric! but seriously, you sound like you have a really nice boat. This is my first attempt to do work for myself, so reality sets in pretty quick. I tossed my calendar as a time line out last year. My only advice is if in doubt, find someone in the business you feel trustworthy and have them give you a second opinion to your own. I am fortunate as I rely on guys I have done bluewater sailing with on many occasions.
I am still working on stripping the engine out and cleaning up the insides while I save $$ for a temp shelter. I need to replace the decks on my 69' CL. Everything else though is mostly cosmetics(not counting the engine) which is why I plug on with it. I really want to get her back in the water and let her run again. On my list, is bright work, new water and fuel tanks, bottom paint, repaint the interior and redo the cushions. As for the rigging, I am going to do a complete replacement on halyards and cables for piece of mind. I know it is going to take a bit, but I think it is worth it.