So sweet Bird. She's really coming together!
But +1 what Hoss said. Just got my beast washed and waxed yesterday for the first time in about a year (yeah yeah I know). Was VERY glad that my flares weren't painted after seeing the scratches, erh, gouges in the plastic.
But you don't really have to worry about that much where you're at right? There aint many long armed cacti that reach out trying to rip you a new one.
I did a fair share of wheeling with my black flares color matched and didn't experience any issues except some gravel chips on the inside lip which i remedied this time around with the white rocker panel urethane coating under the paint on the inside lip. It will resist chipping and even if the topcoat does chip, the coating underneath is white as opposed to dark grey.
As for scratches/gouges on the outer face of the flares I did not have any issues because well, I avoided skinny situations where brush could potentially scratch the flares or pinstripe my bedsides or fenders.
One issue I did have with my black truck was at the top radius of the flare where it meets the fender, some of the paint began to crack and flake due the flares flexing and rubbing against the body. Again, this time around I insisted on the best flex additive available and made sure they sprayed around the inside of the flare to avoid any vulnerable paint lines.
With that being said, yes if you plan on pin striping your rig then color matching your flares with traditional paint/clear without any additional coatings underneath is not going to be ideal. I think Line-X or at the very least the rocker panel gravel coating on the entire flare if you want color matched would be your best option.