I am shopping around for a bike after a long layoff...from dirt bike riding when I was a teenager.

I'm 33 years old now. I've never ridden street except on a street and trail bike from the woods to my house and will be enrolling in a safety course before I buy.
That being said, I had a friend point towards the America. I like what I see and what I've read, but I am worried about maintenance costs. My dad's pushing me toward a Shadow (probably Sabre) due to Honda's reliability record, but I want something with a little more character such as a Triumph or *gasp* Harley. I want something I can grow into without having to trade it for a bigger bike in a year.
Long story short...how many miles does your America have on it and what have you had to repair and what did it cost?
Thanks for the help. I'm really leaning towards the America, but as my dad (Valkyrie Interstate rider) said when I was looking at a Sportster 883, you want to be able to ride it instead of visiting it in the shop.
Kev