Re: How did you get the money for your first sailboat?
I got my first boat by going to the local boatyard and asking which boats were for sale or derelict. I ended up scoring a water/ice filled Pearson 26 for dirt cheap. I drained the water out by drilling a hole in the floor (that I later patched) and it was a great first boat.
Also - I was a sophomore in college at the time. The boat was not "perfect" but it was solid and it was a fantastic boat to learn the ins and outs of "big boat" sailing.