Hi timd, welcome to the best forum out there. I started out my street riding on a Honda CB750 chopped front end, then moved to an 83 Goldwing which I loved for long trips and liked less for the other 90% of my riding. Did some time on a 2005 Honda Shadow and then made the plunge to my current 08 Softail. Got to tell ya, I have ridden some other Harleys (Ultra, RoadKing...) and, for me, the Softail was the best fit. I really liked the 05 RoadKing but for slow manuevers, the wheel felt heavy. The ultra was an older model and it vibrated so bad my wife was determined to never get on another Harley, but she absolutely loves the Softail. Likes the look and the ride. We will be getting a better pillon seat in the near future, but she has no other complaints.
Look at the choices you are set on, sit on them, test ride them, and by all means get some down and dirty opinions. I would look at the self help tips in here for the models you are considering so you can see what some of the common issues are with each bike type.
I have done all the maintenance on my bike and I am a horrible mechanic. The softail is fairly easy to work on and to learn on. Good luck and have a great time in this process. Either way, your getting a Harley...:s