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Re: Small affordable sailboats with ample storage? (planning to live aboard)
Not sore at all, just somewhat amused by the idea of a 23-foot boat with a head and hanging locker. A head of some kind probably puts you into 26 feet, but if you want a hanging locker big enough to hold one week's worth of business suits (or jackets and pants) you'll have to upsize again. Although for three grand you might find that boat, I'd be surprised if it was dry enough to keep those clothes free of mildew. And if you're wintering in Chicago, you'll also need heat. More space and money.
On the three grand budget, and "cheap boats" have been discussed quite often here and elsewhere, you'll be probably buying a boat with an outboard engine, in need of deck repairs, with blown out sails or other problems. it may not be impossible, but a warm dry boat that allows you to live aboard, and still can be sailed or function as a BOAT, is going to be a hard find for three grand.
I know there are "apartments" in Tokyo that are smaller than a 26' boat, but they don't have hanging lockers either, and the head is down the hall, communal style. You will doubtless think it is a waste of good money, but hire a surveyor before you buy the boat, so you have some expectation of how much more it will cost to fix the inevitable problems in a $3000 boat.