Back in 2000 I must have watched over 20 727s get painted at Hamilton on Tuscon airport. It took the main guy and two helpers around 3-4 days to completely strip and paint one of them. They pour this crap on the airplane and the majority of the paint just runs off onto the ground. Then they get out the scrub brushes and more goup and scrub the rest off. This took maybe day and half. The main guy would start taping while the two helpers were still scrubbing. Then the painting started. About another day maybe more if lots of logos and stripes. I talked to the guy, he said his cost was around 30,000 grand for paint, tape, goup, lease of the space at hamilton and the two helpers. the rest was his. He charged around 60,000 grand for plain jane. Upwards of 80 grand for intricate. One of the other guys I knew there said this guy had more money than the rest of Tucson Combined.
I also saw a paint job get wrecked at Miami Intl because the dumbass that was painting it forgot to call the tower to ask what the percent humidity was and the paint ended up sucking up moisture and getting all pitted and runny. It was a 727 for Pan Am. Yes the guy got fired.