My Speedmaster was my first bike (after 15 years of not riding). I think it (or the America) is the perfect bike to learn or re-learn on. Getting a smaller bike like a Rebel or something else small seems to me to be a waste of money. After a month or so, you will be aching for something bigger. The America and Speedmaster are just the right size to always want to ride without that desire for larger. Out of the Bonneville (or T-100), the America or Speedmaster is to get the one that physically fits you the best. The America and Speedmaster (if they fit) are much more comfortable than the Bonneville for longer rides. They both do awesomely for those short trips around town as well.

Soren