I just finished the bike safety class this past weekend. It was a great weekend and I recommend it. Great tips, a little expensive but you can never spend too much on your own safety. Plus the little 200cc dual purpose bikes were fun to whip around on for the weekend. haha.
As for a first bike, I went with the america. I myself would not get anything smaller. I feel the smaller bikes I would out grow quickly. Also on highway riding, I feel comfortable and it has enough power to pass or get out of situations quickly. Whatever you choose for him, he will love it!
