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I've never thought about it on a scale factor. Taking lessons is the way to go. I presume you already know how to swim and are comfortable on the water? Most sailboaters are very particular and will teach you safety as well as technique.
You should be in good shape as you're constantly jumping up to haul this and trim that. Conversly, there are also great periods of time when you need patience as you're going nowhere. You'll need to be a good planner in order to take everything you need with you, no quick trips to the store when you're out there. Being multi-talented helps in case you need to rewire something on the spot.
Get a chart book, very important, so you know where you're going and in order to avoid hazards. Stay out of bluewater and stiff breezes till you know what you're doing. And above all have a very healthy respect for the water and mother nature. She can be quickly dangerous.
I lived aboard for a bit. Sailing is easy to learn. Routine maintenance on a decent sized boat is a *****. Unless your handy and have funds to fix things be careful. I suggest you take a sailing course, then crew for a boat and get the gist of it before buying a boat and striking out on your own. The feeling about being a 100 miles from land at night with a full moon is like going to outer space. Undescribable. Glad I did it, but my maintainence skills kept me from persueing it much.
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