Surly Crosscheck would get my vote (when doesn't it) or one of the 800-1000 dollar touring bikes like the surly long haul trucker, Fuji Touring, Bianchi Volpe, or Jamis Aurora.
Another option is to go used and cheap. Ride something not too great for a while until you know exactly what you want in a bike.
I would not want flat bars myself, thus those ccomendations. A hybrid might work as well. Also, Jeffbeerman's suggestions as far as what else to get are very good.
I know it might sound like alot or a bike, in fact I'd probably erase the idea of saving any money, at least as far as the first year goes, when you have to buy all the equipment. However there are numerous non financial benefits, as you seem aware of
As far as craigslist goes, could you provide us with maybe your height and inseam measurments so we can get an idea of what may fit you?