Gretsch- You are in exactly the same position I found myself and for that matter the other newbies in my class. We all seemed to feel the same way. We were good enough for the parking lot, but weren't all that sure about taking it on the road. I bought a 1999 GZ250 and it was a great bike to learn on. When I bought my Speedmaster three weeks later I didn't have any doubts. I'm sure most of the other 250s would work just as well for this purpose. They all have downsides that nobody wants in the "next" bike, but they are great for a first bike when you want to build your confidence by building your skill level. Good luck.