The sportster is in the cruiser class. Personally I've never been a fan of HD's, I used to have an 83 Honda VF750S Sabre that I had bought in 92 or 93 and just sold two years ago. Hondas are great bikes, good performance, and reliability. My dad's also has a 83 or 84 Goldwing, my brother has a 81 CB 650 Custom, and my uncle has a newer VF750C Magna. We've never had a problem with any of these bikes.
Id you've never really ridden before Find something your comfortable on and look fo something in the 600 to 800cc range. They are much lighter and easier to handle than anything bigger. Most of the japanese brands have bikes that look as good or better than the Harleys (in my opinion) and are much more reliable. A lot of people I know that have bought the sportsters have mentioned the vibration from the engine. You are also paying for the name on a Harley.