Even if you go it alone, specialize to keep your initial investment low. If you do only interior painting, for example, you might get by with one ladder, a few brushes, rollers, basic hand tools and such, for an investment of less than $300. Again, you can add to your tools as you need to (every job is a bit different), and parlay profits into the equipment necessary for exterior painting or working on large commercial properties.
The question, “how is your warranty program funded?” will probably get you some puzzled responses. The fact is, most contractors have never even considered how to pay the expenses associated with warranty callbacks, and some contractors just seem to vanish when they get a warranty call. A professional contractor will be preparing for callbacks (they will happen, even to the best contractors) by including a line item in their budget for warranty work. Ask the question and see what kind of response you get. Sometimes, how the question is answered is more important than the answer itself!
As an owners rep and former estimator for a gc i do expect to pay a reasonable deposit say 10 percent and then weekly progress payments. I am asking the painter to book his time and to do the work on my schedule. Most painting companies are not huge operations they will pay their staff weekly. For most repaints i ask for one tinted primer coat and one finish coat for 100 percent coverage. New work gets one tinted primer and two finish coats for 100 percent coverage. The cost of the paint is not really that different for colors or finish. Brands like european fine paint and C2 are more expensive than Ben Moore and sometimes more difficult to roll based on their consistency. Some home depot brands are as expensive as the Ben Moore and of equal quality others aren't. Red paints are notorious for number of coats required and special priming requirements.