After reading everyone's comments I believe these are the steps I need to take in order to do good at this:
1. Find suitable spray gun (Do they all attach to any regular compressors?)
You really don't need a spray gun for controllers since they are so small, an airbrush will work fine even for base coating them, but if you really want one, check out the Iwata Kustom TH. It's an airbrush that has a fan spray, which is perfect for items like these controllers. The Kustom TH comes with a hefty price tag of about $400. If you can wait just a little while longer, I have heard from a reliable source that Badger is coming out with some fan spray airbrushes for a lot less money then the TH.
2. Find Wicked, Spectra-tex, AutoAir, Krylon and Dupli-Color paint. (Do they come in a giant can or...? and where could you buy them, I can't seem to find them at my local stores except for Krylon/Dupli-Color. I'm looking for all ranges of colors/shades)
Decide if you want to use water based or solvent based paints. I would lean toward using Auto Air as they have some great colors and special effects paint and you don't have to worry about the nasty smell of solvent based paints. You best bet is to buy this online if you don't have a local supplier. I stay away from Krylon. Dupli Color is a little better. You need to find a good clear coat that will hold up. Find a local auto body supply shop and try some UPOL Clear #1 or SEM 1K clear. These are much better rattle can clears then Krylon or Dupli Color. If you can set up a small booth and ventilation, 2k automotive clear will hold up the best.
3. Find safety gear.
Get a good NIOSH respirator
4. Find paint masks to design on.
The paint masks are cut on a vinyl plotter. Look for a local sign shop that will cut them for you for a reasonable price. You can design them in any decent vector program such as Adobe Illustrator, Corel Draw or Inkscape. Save them as an EPS file on a flash drive and take them to the sign shop and they'll cut them for you on their plotter. You need to use a paint mask vinyl. I use Avery paint mask and Oracal Oramask 810. The Ultramask should work as well. Some sign shops stock paint mask vinyls and some don't.
I would also like to know, what kind of paint masks this company uses. I have used them before and they're great.
Assassins Creed - Paint Mask - How to Paint an Xbox 360 Controller
I think it's called "Artool Ultra Mask"?
You can get Ultra Mask from Coast Airbrush.
And thank you everyone for helping me!