The bottom line is if you think you can do it and you've had even a little experience painting... then go for it. Rattle cans of flat and semi-gloss black from the hardware store, painters tape and a shop heater to keep the garage warm and I went to town. That's right I painted the bike myself. It wasn't that difficult given Harley-Davidson did the original base coat, all I did was paint the panels on the tank and rear fender and the striping.
The air cleaner was very easy. I just sanded it and sprayed it. Two or three coats of flat black paint and a couple of clear and I was done.
I covered the Harley logo, then painted the plastic cover and pin striped it.
The tank was a little more difficult but I applied the same principals. I taped off the panel sections on each side (I just eyeballed it and got lucky - I recommend measuring to make each side equal & using a cardboard or plastic template), sanded them down and then primed and painted.
I wasn't sure how to place the decals. This time I decided to measure and try and place them in similar spots on their respective sides. If you look at them close enough and long enough (as I have) I think they could go up a millimeter or so, but who cares.
All that was left was put the seat back on. Done.