I just bought a set of Billboards from a neighbor with only 200 miles on them. He had used the spray-on Plasti-Dip stuff and while it looked okay, it had absorbed the
oil from the rubber and turned the letters sorta tan, and with very little effort I managed to rub a letter completely off with my thumb. So I rubbed all of them off, masked them all, and ordered a can of the Ranger Tire Paint. The Einsteins at Ranger said the stuff was water-based so I thinned it a bit and loaded up my Badger airbrush. The stuff comes out of the can with some lumpy coagulation to it that I couldn't resolve. So, it didn't spray very well, but I did manage to get it working well enough to spray them all with a base coat and then a heavier final coat. I then went back and used an awl to scratch the stencil lines in the letters. They look great and based on how much scratching I had to do to get the stencil lines back, I'd say they will look good for a long time.
It took me about 30 minutes to mask each tire, so a couple hours there, and then 10 minutes to paint all four and clean up. So all in all maybe 3-4 hours.