A small boat is not the same as a small house. Some things are easy to cross reference as being the same or very similar, food and entertainment, for example. Look up the cost of a small house on the Cape and you'll find most are in the $300-400 thousand range. Monthly expenses including mortgage, taxes, utilities, food, travel, entertainment, and maintenance are going to run in the $7-10 thousand per month range or $85 to 120 thousand per year...
A small house on Cape Cod that got pretty small last winter is pictured. For the price of that house, one could buy a heck of a nice 50 footer. For the cost of running the house: mortgage, taxes, utilities, food, travel, entertainment, and maintenance one could have a pretty plush cruise in the pretty plush yacht.
OK, this is a little ridiculous. No head room and some other privations such as no running water or refrigeration, etc, etc. But, it qualifies as small. (And, boy, is she fun to sail.) Let's say a typical 34 footer is going to not break the bank. I read that sailors routinely purchase and fully refit yacht for under $100 thousand dollars and cruise for years at a monthly rate around $3-4 thousand a month or under fifty thousand bucks a year.
Basically, every year of cruising is so much less expensive than living ashore one "buys back" the yacht in few years. After that, the cruiser puts money in the bank each subsequent year... compared to living ashore. If you aren't tethered to the doctor's office with a chronic ailment, cruising is a pretty nice way to partake of retirement or a sabbatical. Obviously, if you have a day job, voyaging is out.
On one hand, why detail the advantages of cruising lifestyle. That's just going to clutter up the harbors. Let's face it: life aboard is just not ever going to cut it for a vast majority of the population. For the cruisers among us, it is a practical way to live compared to life ashore.