Well, look wise I would recommend #1 or #2. #1 would be a bit tricky to be very well done (masking), as #2 is the easiest.
#3 isn't that easy neither, but what you can do it by just wiping the outer line using a cloth with a little of paint thinner right after painting it.
Practically, #3 is the best as when you dismount/mount a tire, the rim's lip will be scraped with tools causing damage to paint. But if you have no paint on the outer line, no harm can be done.
What I recommend is a rattle can painting, as it's easier to be retouched if damaged by offroading or else. That's what I did to my rims, and I didn't even need to mask my tires. What I did was (after removing tires off the truck of course) using a small piece of cardboard cut to the shape of the outer lip of the rim, I held it with one hand covering the tire as I sprayed the rim with the other hand, moving all round the rim, then did the center. I used half gloss black. Just make sure you mask the valve and centers of studs holes which prevents paint from peeling when that part touches studs when mounting tires to truck and keeps threads clean. After you mount your tires on the truck, spray the nuts or buy new black ones (if you spray them you save money and get the same color on them, if you buy new ones, they don't lose color when scratched by tools).
And all this costs almost nothing!

Attached is a photo of one of my rims.

 

Thanks for the info. I'm pretty sure I'm going to be painting them like #2 or #3...now my question is...should I leave the stud cover on or off?

 

you could leave it on, i would use a self etching primer in addition to sanding.
i felt it helped adhere better to the wheel.

 

Thanks for the tip. Would it LOOK better with it on though? They are kind of annoying lol.

 

I would keep it on. If you keep them, you can skip nuts spraying and studs holes masking parts

 

I hated them and left mine off. Didn't look that great but my center caps were so faded and scratched, it wasn't any worse than with them on.

I don't have any center caps on my new wheels either and I think it looks alright.

 

I painted mine with semi-gloss rustoleum. And left the center caps off. I think they turned out good. I'm sitting on a 1.5"t-bar crank and 31" tires.

 

What tires do you have on your truck? What size are they also.

 

I vote blue.