You sound just like me. I'm a first time owner although growing up in the sticks somebody always had some sort of two wheel thing we goofed off on. I have been nothing but happy ever since I bought my 06' Classic. I haven't had to do any mechanical stuff beyond fixing a very minor electrical issue early on and the normal maintenance like oil changes and routine stuff like that.
I bought a few books specifically on the RE's from CMW and they help alot with learning about the norms associated with these bikes.
I'd say that it is a very friendly beginner bike. It's light and nimble, gets great mileage, and it's reliable. Plus the oooh...ahhh... factor every place you go doesn't come with your run of the mill HD wanna be bikes you see every day.
Adam