My second boat was purchased as a sears overstock for $100. Brand new Sea Snark (styrofoam)... For the record, that was 1982. Also for the record, that is STILL being sailed. YEP you heard me, my brother (irony) has it in his possesion, and he had to make a new sail for it about 10 years ago. But the boat still sails, and still floats. It's go about 40 acres of dings in the foam, but it'll never sink! So yeah 30+ yo styrofoam sailboat still working.
My first boat was the same. 1978?? Used. $45.00. Cash from savings. Last seen 10 years ago still sailing.
Same 40 acres of dings.
Then GF, now wife made me a new sail.
Always paid cash for my toys and transportation. All my life.
Posts 2 through 6 are the reality for the most part.
My last boat. Cash from savings. Worked over 325 days a year for 7+ years.
I was pretty lucky for a couple of years. Was making minimum wage and an anesthesiologist had a Cheoy Lee Offshore 32 (?). I got to use it and crew for maintenance work. Such a deal for a 20 yr old eh? Sailing someone else's 100k boat. Heh!
Varnishing the mast on a flat board with no safety line didn't seem stupid at all. Kept you on your toes.