Hey Bill, I think a great first bike for this place would be one of the 250cc dual sports that any of the major manufacturers offer.
Light weight, reliable, easy to maintain, and easy on gas.
They have plenty of power for street riding and short freeway stints and can handle the ubiquitous road construction hazards that occur around here.
Check some reviews for performance (especially braking on pavement) and then check prices and buy accordingly.