My wife and I do ok, but we are far from rich. I sailed off a trailer forever and it is just this season that we are upgrading to a bigger boat with a mooring for the summer and a yard for the winter.
The fees for registration, insurance, mooring and yard come to $220(US)/mo; I know that it isn't that
much money, but it is essentially 'money out the window' as soon as the checks are written. It is as much as a car payment; I don't know how anyone does a boat mortgage AND all the annual fees.
I got into the new boat for cheap, but it wants a lot. It only needs
afew things, however. A tiller comes to mind; I broke the old one trying to see how stiff the rudder was. (I'm quite the brute, apparently)
So, I do all of my own maintenance when I can and I buy used equipment whenever I can. And sailing is just about all I do. No ski passes, no trips, very few dinners out...
It's important to me, so I make it happen.