I had a friend who, tried to, do something similar. Unfortunately he knew almost nothing about boats and bought a boat that ended up costing him almost as much as he paid for it in repairs, sank once, and that he eventually sold for a tiny fraction of what he paid for it a couple of years later having only been able to spent a few hours at sea.
So I guess my point is, if you're going to do something like that, make sure you buy a really good boat.
As a life long sailor, I've seen too many stories like this one. Luckily your friend didn't die in the process, but too many people who think it would be very romantic to get on a sailboat and go round the world don't realize what they are getting into and do.
Just yesterday two men sank off of Nantucket on their homebuilt sailboat and the Coast Guard had to rescue them by helicopter. Luckily they were still close enough to shore to be reached. I don't know what they were thinking, but one of their most egregiously bad moves was bringing 1 survival suit for 2 people. And that is just the most recent story I've seen (like I said, it was yesterday).
There are some great cats like Gunboats or Chris White's Atlantics, but they cost a lot. Can't really compare catamaran's comfort to monohull, since effectively you have 2.5-3 times the living space in a cat.
Dave Barry had a great line years ago; something to the effect of "a boat will end up costing you twice as much as you planned to spend, and you'll end up enjoying it half as much as you thought you would".
I'd say most of these criticisms of boat ownership are nullified when you're actually living on the boat, though. The average boat owner buys a boat, enjoys it every weekend for two months, then every second weekend for the next two months, then every month for the next year, and never gets as much use out of it as they thought they would.
If you're gonna live aboard, though... it's probably cheaper than a house.
I don't think I'd do it myself, though. I'm just not a boat person. If I ever buy a stupid money hole it'll be an aeroplane.
So I guess my point is, if you're going to do something like that, make sure you buy a really good boat.