I recently painted my stock wheels black and they turned out much better than I expected and that's saying a lot because I'm a bit of a perfectionist when it comes to my car. Here's what I did:
1. Take the wheels/tires off the car and clean them really well with soap and water and a scrub brush
2. Sand the wheels by hand with rough sandpaper
3. Sand them again by hand with less rough sandpaper
4. Remove excess dust with compressed air
5. Wipe them off with rubbing alcohol and a clean cloth
6. Mask off the tires with painter's tape
7. Hit them again with compressed air and wipe them one last time with a tack cloth
8. Spray 1-2 light coats of Duplicolor adhesion promoter
9. Spray 2-3 light coats of Duplicolor self-etching primer
10. Spray 3-4 light coats of Duplicolor wheel paint (I used black)
11. Spray 1-2 light coats of Duplicolor clear coat for wheels
I painted both the insides and outsides of the wheels and I bought 1 can of adhesion promoter, 2 cans of primer, 5 cans of color, and 2 cans of clear and I had plenty left over. Masking the tires was by far the worst part for me because it took so long and it was extremely tedious positioning the tape in the gap between the tire and wheel. My fingers also got pretty tired and sore from all the spray painting. I was a little worried when I went to have the wheels/tires balanced because I left the center caps on when I painted the wheels and the tech had to pop them off to put them on the machine, but luckily, the paint didn't chip or crack at all around the seams. I also got a little worried toward the end of the painting process when I applied the clear coat because it looked extremely milky and almost yellowish in spots, but luckily it dried completely crystal clear.
It's been over 6 months and 16,000 miles and they still look great. I noticed only a couple of small chips in the paint, but that's to be expected. I'll probably end up touching them up this spring by spraying a small puddle of paint in a dixie cup or something and dipping a Q-tip or small paint brush in it and dabbing the chipped spots to make them less noticeable up close. I'm curious to see how well the paint holds up this winter. Materials cost me around 50 bucks, if you're interested in a price range. Time wise, it took several days because I really took my time and allowed plenty of time for the paint to dry. It's definitely a learning experience, but if you take your time, they'll turn out great.
Anyway, good luck with whatever you decide to do.