A lot to learn
Sounds like you've already made up your mind, and I hate to say this, but maybe you don't have what it takes to be a cruiser, and what you dont realize is you dont have to have money.
The first thing you have to learn is that if you dont have a big bank roll, you'll have to do most of the work yourself.
I was talking to the wife this morning, the bottom paint around the waterline is starting to show blue. (blue was a guide coat of bottom paint I applied the last time I did a bottom job- about four years ago)over the blue, I applied red--when the blue shows through, put more red on.
Anyway, I'll be taking the boat up the slough to a sandy beach I spotted a while back. We'll ease her into the sand bank as the tide starts going out. we've only got about 3 feet of tide so I figure a foot or so should do it.. as she lays over and the waterline comes out of the water, we paint it... pretty simple, and we've just saved the money for a haul-out. and my boat, its a FIRST 42 from Beneteau.
Your boat as ours and many outhers, is in constant need of repair, of some kind.. either varnish, sanding, repairing or just cleaning up. Hoses break, pumps go bad, Dock lines wear out, and crap get caught in the prop.. Its all part of the boating life..
I've got a maxie prop in my boat, and while cruising in the north-west, I hooked a Crab Pot and wound the line around the prop. So I tossed out the anchor, got the swim fins and mask out and a good sharp knife and put up with the cold water for a few minutes.. after a hot shower, I was good as new, with another story to tell.
As I said, some people dont have what it takes, and some do, The mantaince and repair are all part of the cruising lifestyle, And I think its the pride knowing that keeping your boat in top condition while cruising is a great part of the satisfaction.
And I'll close with this last remark.. we all call it cruising when in reality it should be call " Repairing your boat in Exotic Ports"