I agree with Kelly - buy what you want. If you have a jones for a Harley, then get a Harley. The newer HDs are very reliable. There are lots of used Harley's on the market with very low miles that you can pick up for significant discount. Just be sure that if you buy used, don't get one that has had engine modifications. Get a stock one. I'd say look for anything 2002 or newer. The 2006 and newer models came with a 6 speed transmission, which is something I wish I had.
I would classify all HDs as cruiser style motorcycles. Honda, Yamaha, Victory and Kawasaki all make v-twin cruiser style bikes - those are what I would classify as HD wanna-bes. You could pick up one of those for small money.
There are a lot sport bike fanatics on y/a. There is nothing wrong with a sport bike. They are fun to ride, very fast, great on a twisty road. If your thing is speed, then a sport bike would be a good choice. It all depends on what your idea of riding is. If you have friends that ride, then you probably want to get something in the same style they have - to fit in/keep up/not leave them behind.
If you don't have friends who ride most vendors (HD, Honda, BMW...) have some sort of owners club where you can meet people who ride the same brand of bike as you. If you go to their events, you will soon find yourself with a new family.