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Another consideration as to driving distance is to factor in trips to the boat for things other than sailing. I check on my boat fairly frequently in the winter, particularly after storms. It is not uncomon to find roller furling sails flailing about at the docks after a windy day (I keep mine very secure for this reason). Checking the bilge, making sure the batteries are not dying, looking for frayed lines are all things most of us keep up with when boats are in the water year round. Maintence on a new boat is less, but you will be going to it for some woodwork, cleaning and maintence of the engine etc. We often think these things can be combined with a sail, but friends and spouses are usally not to thrilled about watching me make a mess of the oil filter for half an hour, so I make a separate trip for those things.
I moved from a 15 foot dingy to a 30 ft sloop, and after two years have no desire to go bigger (no kids). What I have now meets our needs, and going longer with added costs etc. does not pencil out. When you get much bigger than 30 feet you are going to have trouble physicaly moving the boat about when docking etc. As you gain experience this is not needed as docking technique improves, but I would second the previous advice about either getting some hands on intstrution, or just accepting that your new toy will get a bit banged up for a while.
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