Re: How did you get the money for your first sailboat?
I had saved money. Then I found a cheap boat that needed significant repair, but otherwise in very good condition. She was a Great Lakes boat prior to coming to the Chesapeake Bay so she had good standing rigging and hull.
Having acquired many skills in life allowed me to do my own work (except unstep and step the mast). Sweat labor is cheaper than paying someone else to do the job. If you can read and follow directions you can do almost anything on your boat. The mistakes are just for learning, and cheaper because you did the mistake. The next time you will not.
1984 Catalina 30 tall rig, bow sprit