Well, it depends on how talented of a painter you are. There is a lot more to painting a car tha just having the correct paint color. It may sound kinda vague, but you have to "know how to paint". That's why I say have a pro do it. You will spend a lot more money fixing it than you would to have them match it. As far as the holes from your wing, weld small metal pieces to cover the holes. That's what I did and it worked very good. You wont have to keep fixing the cracked bondo and stuff.

18 focal g7's
custom exhaust
weapon r coilovers
stage 1 clutchmasters
shaved stuff:
antennae
rear wiper and squirter
spoiler
reverse lights

oh yeah...it's a 99 gs