I have a 2006 Bianchi San Jose for riding in town. It mostly stays in the office for use as an around town bike. I have commuted into work with it a few times, but there is a significant hill climb that is a bear on the SS. And the hill going home is too long and too steep for a SS.
It is a fun bike to ride. In Honolulu, a FG/SS is less likely to get stolen. A big reason it is my town bike, for when I have to lock it up outside for long periods of time during meetings, classes, etc.
Your idea of more than one bicycle is on that I indorse.