Don't get freaked at that "Broken" thread. Some of them are one off happenings. But it's a good heads up for things to check on when you get a chance. Heck, some of them can't be prevented so it's not even that.
The keel thing for instance. If you pulled her one year and found a slight bulge on one side, you'd know to drill it out, drain it out, dry it out, and recaulk the keel bolt heads. That could save you my hassle.
Other things like the cockpit deck drain hoses, all it takes is a quick eyeball next time you're crumpled up in the locker changing your oil.
I feel for you on the back thing, and envy you on the retired thing. Sounds like you and Gabe are in for many fine adventures. Are you keeping the "Pilgrim"? High Flight is "Keel laid" '81 was well, so they're classmates of sorts.