If you want low maintenance, buy a new boat. If you want a low purchase price, buy an old cheap boat.
IMHO, to own a boat and keep it in good condition, you need either a decent amount of time or a decent amount of money. It isn't so much repairing things (normal routine maintenance should prevent things from breaking) as regular upkeep.
For example, my boat was recently hauled for the winter. I spent a day getting the boat ready to be hauled - remove sails and running rigging, remove boom, prep mast to be hauled. When the boat arrived in the yard I spent another day bringing gear home, winterized the engine and water systems, covering the boat, etc. In the spring the process needs to be reversed. Plus the bottom needs to be attended to - sand the old paint, apply new paint. Add topsides and deck maintenance too. So before I sail for a single minute there are 7 or so work days each year.
You also need to consider that gear wears out and must be replaced on a regular basis - sails last up to 10 years, electronics become obsolete, standing rigging must be replaced, lifelines, chainplates, etc, all must be maintained.
In short, a sailboat requires a serious commitment to operate. If you don't have or want to put the time in, you better have the checkbook to write some serious checks. Buying a new boat will make it a lot easier for the first 10 years or so, but then the real work begins.
Deep Blue C, 2002 C&C 110
Mt. Sinai, NY
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