IMHO, he would probably be best to use Indeed or equal to find a job in this area, get his feet wet, and then make his plans for opening his own company. I have no idea of painting costs, and I currently still do my own, at over 70 years old. Also, there is a difference between inside and outside painting. 2 neighbors had 3000 sq ft to 4000 sq ft houses painted OUTSIDE, and as I recall the cost was around $3000, this was 2 coats of paint, one primer, and one final, as well as the second color for the trim and accent areas. I believe this works out to well below $3/sq ft.
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Pennsylvania, for 60+ years, most recently, Allentown, now TV. 
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