No experience with Harleys here, and it's too bad you're late; my brother recently sold his Harley.
Some things I learned from my brother's experience:
1) If buying new, (should be a few used Harleys on estate sale from that Sturges ralley
) it's usually cheaper to just get the standard FXwhatever model and add the pieces you really want than go with a special model. That may have changed;
2) Harleys are called hogs, but they are dogs, so don't forget to budget a few grand for engine and parts upgrades so you can get out of your own way. My brother spent about 4 or 5 grand on his bike (Screaming Eagle intake, Racing Exhaust, Increased displacement, mostly by increasing stroke and not so much on increasing the bore IIRC);
3) If you get the racing only exhaust, be sure and get the one that opens up the exhaust in multiple stages (based on rpm so it's quiet enough to sneak through town and past the cop cars at low rpm, and pass folk without giving them a heart attack on the highway, and still be able to pull hard when you want to - the damn thing sounds like your standing beside a 50 cal machine gun when it opens up.
EDIT: Don't forget to wear ear plugs when you ride.