Re: How did you get the money for your first sailboat?
While in college, I sailed on the inter-collegiate circuit and the family boat, then crewed on a Sabre 34, bought an old GP-14 to teach my new wife, then a Sabre 28, then a Sabre 38. All were bought used and I did my own work - all of it. That was what allowed us to afford a boat. Like Chef, we did this only after taking care of necessities - finishing our education, buying a home, and paying off cars. We also only bought what we could afford to maintain - we sailed for 20 years before we had A/C or pressure water. Also as Chef said, it took a lot of OT to get to this point, a lot of it.
Along with doing our own work, we keep scrupulous track of costs - no hiding anything. That is very important because while a lifestyle, boating is expensive and costs need to be managed. I would say that these two items are the principal reasons why we can afford a boat.
Use OPB's until you can afford it.
Sabre 38 "Victoria"