Welcome to BF.net. Glad to have you on board. This is a very friendly forum with supportive people who are either on the same journey or have been there at one time.
How tall are you? That will help with local suggestions.
I do recommend, though, that you change your criteria from "a good looking" bike to a "comfortable, reliable" bike. I think the Surly would do you well, and is definitely cool, but at a $500 budget, "cool" may have to take a back seat.
I'd suggest you use
www.searchtempest.com. It combines all the craigslists from a defined area into one search. It really helps if you have multiple CL's in your area.
You want a bike that will make that Surly look anemic: