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Re: First Boat Owner Endeavour 32 Over our head?
Where to start. Before you take the boat anyplace, call the local US Coast Guard Auxiliary (USCGAux) and ask about getting a courtesy inspection. This is FREE and there is NO PENALTY if you do not pass. They'll come aboard to check all the safety equipment, give you a list of anything that's missing, and if you've got everything you get a "do not disturb" decal to put on the boat. And the comfort of knowing that you WILL PASS a safety inspection if any other agency stops you on the water, where failing results in a summon$.
Assuming you've got an old inboard engine in unknown condition, you might also want to try (try, it isn't easy) to find a diesel mechanic to come out and check over the engine with you. Diesels need very little routine maintenance but there items that may need adjusting, and he should be able to show you how to change the fuel filters and bleed the fuel system. On an older boat, you may also want or need to clean out the fuel tank, which can be a PITA but a key to a reliable engine.
And you're not even sailing yet. (G)
I'd suggest sailing lessons, and some couples prefer to take them separately. A typical "ASA 100" basic sailing lessons could be three days, split over two weekends, with half the time on the water. There must be some sailing schools listed in Chicago, the USCGAux folks or your local "US Power Squadron" chapter should be able to refer you.
I find a 32 is a comfortable size boat, big enough for all the amenities and small enough so that if you make a mistake, you can still resort to brute force if the boat argues with you. No matter how good the deal, no matter how well you knew the last owners, don't assume that ANYTHING is safe or reliable. Boats have a way of surprising you, and you need to put eyes and fingers on everything. Sometimes a lifeline isn't secure, sometimes the rigging isn't as solid as it looks. There are books and web sites devoted to the mechanics of a boat. I'd suggest finding a couple (swap them) and devoting a good half day to simply starting at the pointy end and working your way back, inspecting eveyrthing up close and making sure it has no problems. Bring lunch and cold drinks, and if your mechanic is as prompt as most contractors, you can do that while you're waiting for him or the USCGAux folks to show up.
You might also want a membership in BoatUS with the unlimited towing option. Not that you are likely to run aground out there--but if something breaks down, a tow back to the docks can be way more expensive than calling the AAA on the highway. Until you know your engine is reliable, along with the sailing parts, that's something to consider.