I've owned a 1500cc Kawasaki, 800cc Honda touring (Pacific Coast), a 750 Yamaha, and I've ridden a 2003 Sportster. Sportsters tend to be loud and shake. You either love it or hate it. How you plan to ride is really important, as Tncobra says, weekend toy or daily interstate commute can be two quite different bikes.
We're headed into colder weather when it should be easy to find a bargain on a bike. I suggest that you buy a bike with the intent of reselling it next spring when the demand for bikes will be much higher than it is now. Follow the other great suggestions in this thread and get a bike that needs no work done on it. In your price range, this is very important because motorcycle repair can be very expensive. If you do this, you should have no problem buying now and reselling for what you paid for it next spring. Asking price is always negotiable unless it says price is firm in the ad. Even that only means that the price is firm right now.
If you like the bike, you can keep it, but if you decide to upgrade or try something different, you won't lose a fortune. I have a 98 BMW F650 that's below your price range that I'll probably sell if I buy the bike I'm going to check out on Friday. Good luck.
Oh, one other idea. If you do an eBay advanced search, there is a check box for "Completed Listings." Enter the bike type you're looking for and you can get an idea of the real market value of these bikes. The various NADA, KBB guide market values are all over the place.
Another approach is to do a SearchTempest search (Craigslist) for Orlando and surrounding cities within 200 miles. Bikes are everywhere in Florida and the asking prices are more realistic. The bike I'm going to see Friday has an asking price of $3,000 but it can be bought all day long in Florida for $2,500. My plan is to try to get the price to $2,500. Don't fall in love with the first bike you see. You'll probably want something else in six months.