Yes, I have wondered several times whether it was a good decision. The Bonnie was my first motorcycle. Fresh out of the basic rider training, I saw a photo of a friend's Scrambler, and he suggested the Bonnie for me. I bought the bike, had her delivered, and then headed out for my first ride. I loved it. On the fourth day I was trying to make a turn from a stop sign, the clutch slipped, and the bike died on me, and I went down. I was embarrassed as hell, and frustrated. After getting out of the road, I sat on the seat for a bit and just kicked my own ass for a few minutes. After I calmed down, I rode home with no issues. A few weeks later, after breaking my wrist in a bicycle accident, I slipped and dropped the motorcycle in the garage. I was certain at that point that I had purchased too much bike for a first bike. I also had vertigo problems at that point, and after those were resolved, I had no confidence that I could ever ride any motorcycle. That all happened between July and October 2008.
Fast forward to March 2009, I am tired of looking at this (scuffed) piece of machinery in my garage. I took the intermediate training, found a local rider with lots of experience who was willing to help a newbie, and in 3 weeks I've added over 300 miles. A new set of handlebars, new mirrors, and a Dart screen, and I feel that I can do this riding thing, and that I have a good bike.
In hindsight, I questioned whether I bought the right bike. But, at this point, I think the problems I had were due to trying to do too much too soon. Bonnie, FZ6, CRB1000RR, Honda Rebel, I don't think it would matter.
That's a really long way of saying, yes, I did question it. But, at this point, I could not be happier that I got the Bonnie.