Tilting with windmills
Join Date: May 2008
Location: North Texas 'Burbs
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Welcome to the forum Rev.
I'm mostly a road bike kind of guy, so I don't have a lot info on selection for you. You single speed inclination limits me even further in what help I can be there.
It sounds like you might be best served by a Hybrid, or hard tail mtb, except for neither one being SS. Another option might be a flat bar road bike if it's able to accept a little heartier rims and tires.
Honestly, your description sounds ideal for a cyclocross bike, but you would have drop bars and gears. This could be remedied with a set of trekking bars from Nashbar for around $20. I'm not sure how the shifters would work though. A cross bike would have everything you listed as far as great on the road, can do trails, and curb hopping is encouraged! Most models come with eyelets and braze ons for racks and fenders as well if you want to use it to commute.
One thing to remember about drop bars is that you don't necessarily have to ride in the drops. They give you more hand position options and you can always ride the flat part of the bar or ride the hoods of the levers. Most of use the hoods a majority of the time I think.
Edit: Forgot to add that your budget allows for a pretty nice bike with year end clearances upon us. You should be able to get a lot of bike for a good price, no matter what you choose.