I've recently seen boats as cheap as $5,000 that 'looked' serviceable but insurable? Check craigslist- people are giving away sailboats (not in great shape).
It'll cost you $1,000+ every year to insure a boat depending on where you live.
Go cheap, go small- Look at Dave and Jaja Martin. A family
of 5 on a 30 foot boat and before that they had a 27 (?) foot boat.
We live on a 33' boat right now with our infant daughter.
We are new to living on a sailboat- we really just started before Christmas
. This first several months have really been about learning
what is important on a boat and how to function (including where to put all the stuff).
One thing we've learned so far. There will always be things you'll need to do the boat to make it safer and there will always be a long list of maintenance- regardless if it's a $5,000 used boat
or a $500,000 new boat.
Another great maxim- "You don't know what you don't know, until you know."
We've owned our boat for about 4 years before moving aboard, we thought we understood what was important and everything there was to know about the boat. But priorities change once your actually on the boat. Unless you have a ton of experience, why not buy a cheaper, smaller boat that is easier to handle and you won't have a coronary when you run aground (and you will) or scratch the gel coat.
Everything is cheaper on a smaller boat- fuel
costs, sail costs, haul outs, bottom jobs. Consider the 'whole life' cost of the boat before you break the bank to buy a 50 footer.
We own our boat outright. In todays market our boat is worth about 25-30k. So we picked up liability insurance
and bought a bigger anchor
I really think you could find a classic late 70's to early 80's fiberglass
boat in the 30ish foot range for cheap and with two quarter berths and the salon- there would be enough bedding for the whole crew.
Best of Luck