Re: How did you get the money for your first sailboat?
This will sound like a bad idea, but it's what I did...
Maxed out my 401K contributions for a couple of years while I figured out what I wanted and then took a 401K loan. At the time it seemed that my tax deffered savings was better than a bank account or savings bond. Better than trying to finance and older boat that I could have only gotten a high interest personal loan against. It worked out for me.
I got lucky, took the loan when the market was in great overall shape and new sailboats where selling faster than they could make them. This was a trade in for a new Catalina and the dealer just wanted to get rid of it before they had to start paying winter storage/haul out. So I got what I consider a very good deal.
The market soon tanked and I paid most of it back through a recession. That is not to say that it will always work out that way.
Fast forward 11 years and I sell the 40 year old boat for about 80% of what I have into it (not bad for 11 years of fantastic sailing) and use the money to put down on something newer and shinier.
Plus I made some great friends in the process of selling it.
Like I said, a bad idea that worked out well for me, but there might be better ways to do it.