I made the HUGE mistake of hiring Certa Pro to do several interior rooms of my house, and remove popcorn ceiling in a bathroom. What a nightmare! They didn't paint any door jams, they broke a cedar window sill-and didn't bother telling me, they gouged a hardwood floor, they never sealed the room that had the popcorn removed--causing white powder to be in all rooms of a 2 story home. I can go on and on. Horrible company
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.
A professional painter will help you select an exterior paint designed for long-lasting results, superior protection, and ample coverage. Higher quality paint requires fewer coats and lasts far longer, saving you money down the road. Oil or latex paints in a flat/matte or satin finish make excellent choices for the exterior of your home. These paints will endure extreme weather conditions, can be customized to your specific climate, and are ideal for painting siding.