Even if you think you'll probably do the job yourself, it's good preparation to seek estimates from professional home painters, whether your painting the exterior or interior of your home. Then you'll have a financial point of comparison and you may benefit from what a home painting contractor has to say about the condition of your home, color choices and types of paint available. Let the painter make his pitch for a professional job before you decide what to do. You can still opt to do it yourself while having learned something worthwhile.
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.
Maybe you've just moved into a new home, and you haven't got around to buying brushes and rollers yet. Perhaps you're worried that your brush-skills aren't that good, and you won't achieve that professional-looking finish that you’re really going for. Handy professionals will turn up with everything they need to get the job done, from ladders and brushes, to rollers and tarps. You just have to provide the interior paint and primer!