I started sailing last season after not having sailed for nearly twenty years (on a 420 when I was about twelve). I bought a second hand boat (Tomcat from Stealth Marina, 16ft, no daggers, very light and easy to right, 10m2 main, 3m2 jib, 15m2 spi) with a friend and joined an extremely friendly local club. The boat was probably the right choice (rather luck though). Very easy to handle and not too much sail area. However, the key was the support of the local club. I was amazed by their friendliness (as stated in another response). They never gave me this newbie feeling and helped me out with the most stupid questions. Join a club and try to crew for a couple of sailors with different boats. You will quickly find the boat that is most attractive to you. Another benefit from joining a local club is the safety boat that is always out there when we sail (don't know if this is the case with all clubs). It gives you just a bit more confidence to try things, knowing that if everything goes terribly wrong, you will get help. Rick's and Mary's book were extremely helpful, too. Simple language and very thorough.
You're warned again about addiction. I got so addicted, I wanted more. The boat I bought didn't give me enough tuning opportunities and was not fast enough. After having talked to a lot of guys in the club and read many threads here in this newsgroup, I came up with a detailed list of questions to help me to find the right boat:
- do you want to sail single handed, double or both?
- what will be your typical crew weight?
- are you keen in a light boat (below 130kg) or does weight not really matter
- are you interested in class racing
- will you sail in a light wind or heavy wind area
- are you planing to trail your boat a lot and do not fancy to disassemble every time (limits width to about 2.50m)
- price willing to pay? new? second hand?
- local dealer & support for spare parts?
- racing against the same boat/class is much more fun than using handicaps - what boats are sailed in your area?

I bought a second hand F18 (Dart Hawk) in December. To be honest, I was scared the first time I went out in January this year. Everything reacts so fast and the speed is incredible. However, the skills I learned last year helped me to make this step (similar to Jake). I can tell you, it is so much fun!!!

Hope this gives you a couple of ideas from a nearly NEWBIE.

Happy sailing.
Phil