Reddit mentions of Boatowner's Mechanical and Electrical Manual: How to Maintain, Repair, and Improve Your Boat's Essential Systems

I learned a lot from Power Squadron classes, but that was more about navigation and safety than maintenance. Very useful however. It will put you in touch with a bunch of great folks who will love to chat maintenance. Other than that, I got the Nigel Calder book (http://www.amazon.com/Boatowners-Mechanical-Electrical-Manual-Essential/dp/0071432388/ref=sr_1_1?s=books&ie=UTF8&qid=1373317120&sr=1-1) and chatted up everyone in the Marina.

Also check out the Wollaston Yacht Club in Quincy. It's got a bunch very cool down to earth folks who love boats, boating, and maybe beer.

If you haven't already grabbed this or this, I can't recommend them enough as excellent resources to address this and many other questions.

Best investment you can make! Everyone should have this on their boat! http://www.amazon.com/gp/aw/d/0071432388?pc_redir=1397569458&robot_redir=1

Check out a couple of books by Nigel Calder. I recommend starting with Nigel Calder's Cruising Handbook as it's a pretty good general overview of everything you need to know for cruising, then try Boatowner's Mechanical and Electrical Manual as a guide to all of the stuff that you will spend all of your free time fixing and maintaining. I also have Marine Diesel Engines. He does a great job of explaining everything you need to know in an accessible way. He manages to get to some pretty advanced skills without assuming very much previous knowledge.

https://www.amazon.com/Boatowners-Mechanical-Electrical-Manual-Essential/dp/0071432388 This will help you fix nearly everything. It's slightly technical but has very good information.