Just remember, that boat maintenance, as a rule when done properly, gets lower rather than higher. If you do the preventative and proper maintenance, the big costs generally are avoidable. Bringing a boat up to spec, after a long period of questionable maintenance takes some doing, regardless of what boat it is.
I would highly recommend you read the Boat Inspection Trip Tips
thread I started, as it will help you get a real baseline on what is needed with your current boat.
If you like the way the boat performs, sails and looks... there's no reason not to go ahead an invest in the boat, provided she's basically sound to begin with.
Looking at a boat from a purely financial perspective is ridiculous...since any financial perspective is going to say that not owning one is the only thing that makes sense. They are a financial strain any way you look at them, even if brand new.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.