Soren,
I did just that! After 25+ years without a bike I took the motorcycle safety course and bought a Honda Rebel 250 to hone my limited skills. After 17 months and just over 4000 miles I felt ready for a change. I went to the guy that taught my MSF course and asked his advice on a larger bike.
He said to get a Triumph America, I would never regret it. 6 months and 7000 miles later he was right. Mine does qualify as an "upgrade" and the little Honda was a good reliable choice for my needs. I'm 64 and the America,2009, has been written into my will for my sons in 15 or 20 years!