As regards overcoming the whole start and stop thing I have found that having a goal is a great motivation. For me this came in the form of Tour-de-Cure. (I completed my first tour this weekend, I'm still prepping for the Tour-de-Cure)
The nice thing about the Tour-de-Cure is that they are not a competitive events, have lengths from 5 to 62.5 miles, and they want you to be successful. As a result they provide training rides. It can be great motivation and you learn a whole lot.
I'm sure something of that nature would work for you too.
It looks like the closest to Milwaukee is the Southeast Wisconsin Tour de Cure in Grafton.
If you are interested in something like this then you might visit http://tour.diabetes.org or google for another