Thanks for all the replies.
Good news. I picked up a bike today. Grabbed a Trek 700 multitrack from a pawn shop for $60 bucks. Money left over for a few repairs/maintenance. It's a little rough around the edges but it rides good. The bike is exactly the style I was looking for. So for $60 bucks how'd I do?
And here's a little story from today. The college town about 45 miles from me has a non-profit bike "shop". They cater to people who have a need for a bike and the folks with limited finances. It's a pay if you can type place. I went in, reluctantly, fully prepared to pay what I thought was a fair price for a used bike. I saw the owner take one look at me, my wife, and 9 month old son and knew he was unhappy. Told him I was looking for a used bike. He tells me he helps people who are in need. I tell him I don't mind paying a fair price for a bike. And he names another shop I could go to. He then tells me to go to bikes direct and spend $400. And proceeds to tell me I can spend 400 because of my nice sunglasses, which were a gift, and that he's a hardass and has ridden to Boston from Florida 15 times and just how awesome he is in general. And pretty much just tried to make me feel bad for not being flat broke and trying to find a cheap bike. All I know is he was a real a-hole. Surely this isn't typical behavior for this type place is it? And their website says they are "dedicated to providing reliable transportation to anyone who enters our door".