having bought our first boat, Jibberish, a Catalina Capri 16.5 last winter when ice covered all available fresh water lakes in NH where I live. Some ideas? Read absolutely everything you can get your hands on. I read the major sail magazines (Blue Water Sailing, Boat Works, Good Old Boat, Sailing, Small Craft Advisor...to name a few). I purchased K.I.S.S. Sailing/Sailing for Dummies to provide a simplistic overview of the sport. Reading about sailing before actually sailing prepared me mentally and equipped me with the vocabulary I needed to understand the advice I was receiving from others. My husband and I had joined a college sailing club 15 years ago when in FL. We learned on a Laser. I highly recommend sailing the smallest vessel you can as a beginner. I find it hones your skills more sharply as you learn the effects of your actions on the boat's performance. Some sailing programs have you tip the boat in a controlled situation so you lose the fear of going in the drink and gain the skills needed to right the boat. I highly recommend this. As to money...boats can be borrowed, rented, or bought for much less than you think, especially smaller ones. Ours cost $2,ooo.oo and we could have sold her for more than that after sailing her for a year. I'm not sure as to your circumstances, but you might also consider looking to crew a boat after learning the ropes. Join and network within a sailing club near you. Opportunities can arise in the most peculiar ways. Much luck to you. My family has found sailing to be the most enjoyable way to see the New England region and, someday we hope, the world!
Resa