I have never painted any for outdoor, but any indoor speakers we just request a pint of paint from the customer. We actually have a spray booth at our shop and air system left over from the car audio days of sunroofs and custom enclosure making that I use. I bought a small automotive touch up gun from harbor freight and use that. We usually keep the extra paint for the day of install and keep a small brush on the truck for touch ups and scratches. We charge 25-50 a speaker depending on the PIA factor. If you have the area to set it up like described above in other posts with everything all layed out it's really easy money.
One thing I have learned in this industry. It is easier to pull a wire than it is to push one.