I know that there is a forum here dedicated to SS/FG, but from what I can tell, the usual advice is to either a) buy from BikesDirect or b) convert an old road bike.
Though there are hills around here, I've picked a few different routes that I use that avoids the biggest elevation changes. I have more issues with the wind, but again, I have different routes that minimize the time/distance battling it. I'm multi-modal (bike/bus) and use a backpack.
I realize that gearing will boil down to a personal trial and error thing, I could use some help in selecting a decent entry level SS sourced from the LBS. Problem is that the LBS push the mid level price point models or don't even stock SS/FG at all. The following are ones that I know I could order locally that are within budget, followed by some that are interesting but lack pricing info.
-KHS Urban Soul- Not exactly enthused about the fork, and the ride might be somewhat of a shock, as I'm used to 26x1.5's.
-Giant Via 3- Do be honest, if I went with this frame, I'd probably opt for the Via 1 to get the goodies and IGH.
-GT Traffic 5.0- The shop I have to order this one through claims it would be a special order, and they aren't thrilled with the idea of taking it back- even for an in store exchange.
-Redline 925- Another special order through a different shop. They would charge me a restocking fee if I returned it. Pricing info not listed, but aside from the pathetic fenders, I think this one appeals to me the most.
Again, I'm multimodal, so I need something that will fit on the Sportworks racks the buses use that have a maximum 44" wheelbase capacity or that I can lock up at the bus station all day and not worry about it. It's kinda hard to shop without test riding, but it's also hard to test ride when the LBS don't/won't carry these models...