Bill, I live in western Henrico, too, and day sail on Swift Creek Reservoir. Sounds like you're eventually thinking Chesapeake, but if you want to quell the jones in the meantime, I'd be happy to have you aboard sometime.
My answer to "what first cheap small simple reliable roomy compact easy to handle fun safe comfortable boat do you recommend" is a Flying Scot. But that's only one of a bunch of reasonable choices. If you'd like to get out some weekend or evening for a Scot introduction, send me a PM.