Thanks for all the good advice. I've joined a club and have got out a few times already, but I'm keeping my eye out for my first boat (cruising the marinas, ads, ebay

and craigslist etc) The club also has Thursday night races, which I hope to start to take part in next week to get a feel for the casual race atmosphere. From there I want to look into crewing in other races to get some different perspective, different boats etc.
FWIW, here are the problem areas of the cheap-sail-her-into-the-ground boat...