Re: How did you get the money for your first sailboat?
First sailboat: Catalina 13. I was in college (only 7 years ago), had been making money posting ads to help people move couches/refrigerators/whatever with my brand new pickup truck. $30/hr and booked my weekends doing that for cash. $1,000 for the Catalina Capri 13 Cyclone. Sold it for $1200 once I got a weekend part-time job and was still in college, but had no more time for sailing.
Second Boat: Prindle 16. It cost me $0 because a friend needed to sell it due to him moving. Although, I immediately put about $1500 into it, then sold it 2 years later (well worth the $$$ for the memories) for $600. I told myself I'll still pay him the $300 he had been listing it for.
Third boat - Current: Catalina 30. I had saved and earned the cash from 4 years of valeting cars while in college, and managing a small company. At the tippy-top of my budget, its cost was $15000 from a list price of $24,999. But we all know, just purchasing a boat is expensive. $1000 for 2 surveyors (boat, rigging) and a haul out to survey it. $1400 to register it. several hundred for immediate upgrades to expired safety equipment and cleaning supplies. A couple months later a bottom job, a stuffing box repair, I was probably drained of $18-$20k since purchasing it in September.
Thankful for a credit limit and steady income.