Re: How did you get the money for your first sailboat?
I think my situation is not the norm, but I'll tell my story anyway:
I sold my townhouse inland, and bought a detached, single family home very close to the water, in a "water access community". Basically, that means that at the end of my street is a private beach and boat dock. I pay a small annual fee to use them.
I decided that since I had a dock available, it would be a shame not to fill it with a sailboat, so I took $2,000 of the townhouse proceeds and bought a good "training" sailboat off of Craigslist.
Fast forward two years:
I sold the training sailboat for a little less than what I paid, I sold my DeLorean and my motorcycle, and bought my Pearson 30. I didn't have to sell all of those things to meet the purchase price of the boat, I sold them to buy the boat, pay off bills, and have cash to upgrade the boat to my desires, and maintain it the way it deserves.
I'd sell pints of my blood to keep the boat.
S/V Old Shoes
1973 Pearson 30 #255