Harleys suck. Overpriced and overrated old technology crap. Get a rice burner, they'll run forever; I have a 2000 Honda CBR 600 F4 with 41,000 miles, never had a wrench to the engine... other than to check valve clearances of course.
First thing you gotta do if you wanna ride is take a MSF rider safety course. You'll get a break on your insurance, and when I did it, we took the riding test portion at the end of class, didn't have to do it at the DMV.
Always wear safety gear, helmet/boots/jacket/gloves. You will crash your first bike. I crashed mine, my brother crashed his, we had our gear on and walked away without any scratches. It happens, mainly due to inexperience and/or stupidity, but you'll learn from it and won't ever do it again...
Buy used for your first bike. Take a look at the Suzuki SV-650, they're a very popular "beginner" V-twin... I've never ridden one, but have heard that everyone that rides or owns one loves 'em, great handling and performance, and there's plenty of used ones available for decent prices. If you wanna go the sportbike route, may I recommend a used Honda CBR 600, an F3 or F4 maybe... they have all the performance you could want, but they're very docile and won't bite unless you really push it.
Just my humble opinion of course... and did I mention that Harleys suck??