Don't buy a cruiser. Take your $1000, find a used Japanese standard, and learn to ride (assuming your're new at it, of course). IMO, starting out on a cruiser will cause you to build a bunch of bad habits into your riding technique, due to bad feet position, bar position, and the performance capablity of the bike itself. Then if/when you get a Buell (or other newer, sportier-style bike), you'll have to un-learn. At $1K, you're going to be buying mechanical shortcomings no matter what you get, so at least with something semi-current (Honda 599, 919, Nighthawk, Kawi 750, Yam FZ6), parts are pretty common, and the performance will be enough to keep your interest. Plus, you'll probably be able to sell it easier than a cruiser and still get almost all of your money back.
Back in the dark ages, my first street bike was a Honda 175. Rode it everywhere, and continued the wrenching learning curve that started with dirtbikes. But I'm off track. Go with substance and develop your own style. Don't waste money trying to buy style.