Don't get the 883, get the big Nightster 1200; this is the baby Nightster. Wait til you see it in person. It's tiny. Even I thought it was on the smaller side when I got on one at the bike show; the regular Nightster.
Ryan do not get a glorified sportster PLEASE!
For that money you can build a sick custom put it together yourself bike....with a REAL Harley motor.
Check out "Zero Engineering Motorcycles" under Google.
+I'm about to sell a bike with a similiar look you might like, to get your feet wet.