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If you have a partner/spouse what they feel comfortable with is a starting point. This is easier if you've been renting or chartering a bit.
Make a cold hard estimate of how you will be using the boat. Often we buy boats based on infrequent use e.g. an annual multi-week cruise as opposed to weekend or evening sailings. It would be less costly to charter for those infrequent uses, and allow more cruising variety as well. Smaller boats appear to get more use than bigger ones.
If your analysis gets you to a trailable boat this is a big cost savings. Marina fees add up. The ability to do maintenance in your yard is far more convenient and less costly that on the water. You can take an outboard to a shop whereas you bring the mechanic to the inboard $$$.
Most boats have a depreciation curve steep that's like cars steep at first then flattening out. You can see this in the blue books. Age however doesn't affect sailboats all that much. Often owners pour a lot of money into upgrading thier boats that they never get back making an older boat better than its new cousin. Electronics are usually outdated in about seven years however. diesel engines need to be checked by an expert. You can do early damage to diesels by not running them properly.
Buying a popular class boat has advantages in info on how to deal with class problems, easier to sell and contacts and info on available boats.
Finally, if getting an older boat, make a good estimate of what the upgrades will cost you. Usually hunting down a well loved boat that has that stuff done is a better strategy.
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