Ok, can we get back to the issue at hand? 
I don't know Chip, or where to look to see what performance mods he has done.
This is my opinion, and the simplest approach to your questions: Put the stuff you got coming on there, get a good tune, and see how you like it. You'll probably be pleasantly surprised at the increase you get in "seat of the pants" riding pleasure. If that's not good enough for you, or if in a few months you get used to it and want a bit more, I would put a set of either Zippers or Freedom bolt-in, gear driven cams, which require no head work, just pushrods, better lifters if you want them, and maybe checking the clearances on the rocker box covers, depending on which cam you use. IMO, either of these two cams give the most bang for the fewest dollars spent. If you do the work, you're talking under 1K. If someone else does the work, then still around 1500 or so, as the cam swap is not a labor intensive job.
Is there a hell of a lot more you can do...yes! But how deep are your pockets, and how much power do you need? If your goal is to chew up almost everything you run into and spit it out, then get ready to spend a chitload of money, pull the motor out, split the cases, add better support bearings, bore the cases, add jugs, get new heads, different cams, different rocker arms, better springs, bigger throttle body....the list could go on and on.
On the other hand, if you want a nice, powerful ride, that can outperform 80 or 90% of most the HD's you'll see on the road, do the cams. Don't forget to spend some money on better suspension to get the power on the ground in something besides a straight line, and some better brakes or pads to get the damn thing stopped after you've twisted the wick.
That's my 2 cents and is the approach I'm personally taking.