I set a goal to do as much riding on my SS as possible this spring and eventually going all-out fixed by the summer. I currently ride a Windsor Tourist as my full-time commuter. Its a heavy hauler, geared low, etc. The first mile of my work commute is uphill. I will admit I could be in better shape, and could loose some weight myself. This being said, my one and only SS/FG is currently geared at 44/18T. Should I gear this a bit lower as I acclimate to SS riding? Or just tough it out and take my time on the hills? Or am I being unrealistic in what can be done with a SS/FG machine?

I welcome any comments or encouragement.