I would only purchase the bicycle that felt best when riding. I would never settle for anything less than the best possible ride that my money could afford.

Therefore, I vote for the CAAD X and some type of good rapport with some LBS. If there's a bicycle co-op nearby, then depend less upon external bicycle repair sources. Instead, become more mechanically independent! Just have a good rapport with a least one LBS, for the few things that may be beyond your skill level.

PS.

I agree with Bikemig with regards to locking your bike up for extended periods of time at some frequent location. Bike theft would be my primary concern while working...

IMO, a used bike would be a better option...