These are some fantastic questions to ask and I particularly like the one that is concerned about safety for the painters. After all, if you have a large home and you’re hiring them to paint the exterior of that home then they’ll likely be on scaffolding. Because of that, you need to make sure that the contractor not only provides appropriate safety training, but has the correct liability insurance as well.
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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.