I have been riding on the street since the 90's. Mainly sport bikes. About a month ago I purchased a 2011 FLSTSB Crossbones, gloss black. I absolutely love it. Best street bike I have owned and the only bike my wife has ridden with me on. I looked at the Street Bob and Wide Glide but decided on the Crossbones as this was the last year model for them. Springer front and bobber seat. Doesn't get more unique than that.
Second piece of your question, Motorcycle Safety Foundation should offer classes in your area. I completed this when I began riding on the street and what you learn is invaluable and may save your life one day. That said, Harley offers programs for new to motorcycling owners.
http://nm.msf-usa.org/msf/ridercourses.aspx
http://www.harley-davidson.com/wcm/C...rn_to_ride.jsp
Riding is one of the most liberating things IMO.
Pics of my new bike:
