PT I think you're making a good decision. While rejetting isn't brain surgery it does require some mechanical skill to get the carbs off. I don't know how far you plan on going with your modifications, but you might want to consider doing away with the air box eventually, which will make changing jets a snap. I'm a far cry from a mechanic, but I've managed to remove my air box and go with pod filters, and now I can rejet in about 30 minutes. You need a decent set of tools, but they're not that expensive, and you probably want to get a set of hex screws to replace the screws that hold your float bowls on. It makes things much easier.
I've found this little twin an easy engine to work on, and when I take my time and think about how to go about it I can do most of the maintenance myself. Lee is right, some things should be left to the professionals, but the more familar you are with your engine the more confident you become and the easier it is to do things yourself.
Just my two cents worth.
08 America, Bub slip ons, A/I removed, emissions "stuff" & air box removed, billet intakes, UNI Pods, rejetted, carbs balanced, intminators, Progressive 412's, 1" risers, Corbin seat with driver back rest, TP USA Option 2 Igniter, 813 cams