It depends..retire on Lake Erie it's too cold for 8 months out of the year. Retired should mean less ties of course grandkids factor in too!.. I'd get a boat at least 42' mono or 38' cat all fiberglass decks etc., roller sails mail and head sails or at least lazy jacks. power boats are easier to run as long as the engine is in good shape and you have money for diesel! Live abroad on a small mono can be confining, dark, cold, wet/musty, etc. to say the least especially in cold climates. Having the right creature comforts is important..heater, dehumidifier..sun light below...large enclosed cockpit..we're talking cold climates right??? ;>)!! I'd move to the BVI and sail the Caribbean 42" min and a 40' cat for real live abroad space and comfort.

IMHO.