I had an inquiry from a man who wished to take classes on how to maintain a boat. Then I scratched my head.
When I was 20, we were in the middle of the Caribbean Sea days from land. With five onboard, I was the most experienced sailor. The owner came up from below to report that the bilge pumps stopped working and rather than continue to our destination, we would turn and make a run to Venezuela instead. I said, "Give me 20 minutes." I went below with a screwdriver, disassembled the bilge pumps, cleared wood chips out of them (new boat) and got them all working 100% in no time at all. We continued to our destination.
This wasn't hard, nor difficult nor took any particular skill. Familiarity did help having stripped down bilge pumps before replacing worn parts.
My own experience is just from hanging around boats my whole life, summer on the water, winter in the shipyard. I know the answers to what you're looking for as those traditions have been passed down to me by the various experts who do these things for a livelihood.
Even when I step on other's boats, immediately I see things that lack in maintenance, I don't even hesitate and get the tools and supplies to fix them immediately. It could be as simple as sewing some canvas back together (needle and thread), checking the oil level (transmission too), etc. I SCUBA dive and have removed cigarette filters that have been sucked into the water intake for engine cooling (twice). I pulled a broken propeller shaft and installed a new one. Pulled a broken propeller on another boat and replaced it. Boats need just as much attention as a house or a car.
How do you learn to take care of a house? How do you learn how to take care of a car? Same sort of thing. You pick it up as you go. Unfortunately, sometimes it is forced upon you at the most inopportune times! The engine dies as you are trying to get back to port. A halyard breaks dropping the sail into the water, etc.
Some call me "McGyver" because when things fail, I'm aware of everything that is available on the boat, and can quickly come up with a quick fix that will work until we get ashore to get replacements.
The area I suffer the most is with engines. Example, we sailed down the lake in big waves, the wind died and turned on the motor, not too long after the engine died (20 miles to get to port). Being a diesel, everyone tells you they need "air," and they need "fuel." It is very simple. I check the air filter - clean. I check the fuel filter - clean. They say that connections can loosen on the fuel lines allowing air to get sucked in, which kills a diesel. I take a wrench and tighten all connections from the fuel tank to the engine. Nothing I did would get it running. We limped slowly in light winds into port.
The next day the mechanic comes, hears our story and says, "I know what it is." He goes to the fuel tank, loosens the fuel line, pulls it away and fuel is not coming out of the tank. He takes a pencil from behind his ear and pokes it into the tank, fuel starts flowing and he puts the fuel line back on. That's all it took. The manufacturer of these fuel tanks has installed a screen on the inside of the tank where the fuel line attaches. Completely not serviceable. The mechanic explained that the screen is unneeded, and the fuel filter on the engine is there just to do this job. And we should replace the fuel filter on the engine in a month after the debris in the fuel tank has a chance to work its way to the fuel filter.
So there is one kernel passed down, probably not needed, and how does one teach that, and all other examples in a classroom setting?
After typing for a bit, there are maintenance classes that I have thought of. At the boat show at McCormick Place, there are seminar rooms http://www.chicagoboatshow.com/. Look at the schedule of seminars to see if any of those work. They also host on the show floor a thing called "Fred's Shed." Mechanics take turns answering the audience's questions, running scenarios, explaining engine and transmission maintenance, etc. Two years ago I spent 20 minutes with one of the guys between sessions, and they convinced me not to buy a small powerboat to fix up, that it would cost a lot more than buying one in decent shape just about ready to go. Then Crowleys Yacht Yard runs what they call the "Yachtapalooza" http://www.crowleys.com/YachtaSeminar2015.html with seminars throughout the day. Engine mechanics, riggers, fiberglass technicians, etc. all take turns describing the normal types of things they run into.
Then there are pieces and parts of boats described at other seminars.
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