What area of the world is he going to be in. Some parts are fairly expensive, and living aboard even a 28' sailboat is going to be at least as expensive as a small studio apartment.
This is possible, especially if he is in one of the more southern, warmer climes, less so if he is north of the Mason-Dixon line. The main reason I say this is that living aboard through a cold winter can be very difficult without a well-equipped boat.
Also, what kind of skills, aside from sailing ones, does he have. Can he do fiberglass repairs, electrical work, etc. If he does not have the mechanical aptitude and a can-do work ethic, then fixing up a boat may also be well beyond his abilities.
How old/mature is your son? This is a lot of responsibility, and many who think of doing this do not have the maturity or level of responsibility to handle it. It is far more responsibility to live aboard a sailboat than it is to live in an apartment. There are additional risks and challenges to living aboard, that do not exist when living in terrestrial housing—like storm preparation, etc.
What is his budget for purchasing/maintaining a boat? That will often determine what boats will be available to him.
A few good smaller boats: Contessa 26, Cape Dory 25, Alberg 30, Pearson Triton.
Just remember that the costs on a boat go up with the length. Moorage, docking, storage, and maintenance-related fees are all generally charged per foot in some way. Also, the cost of the equipment, such as sails, running rigging, standing rigging, winches, also are generally higher, as larger boats have larger sails, rigs, and winches. Maintenance-related costs also generally go up with the size of the boat—power washing, hauling out, amount of paint needed, etc.
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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.