Work with a professional painting contractor. If you haven’t done so already, sign on to work with a painting company near you. As part of a professional team, you’ll learn the tricks of the trade and work in a variety of different environments, both commercial and residential. There’s no better way to accumulate practical experience than to do it on the job.
I have used Flying Colors in the past for roof cleaning and refurbishing and painting my cedar siding. They did an excellent job then so when damage was done to my roof due to a fallen tree I immediately thought of them. I called and within a day they had someone out covering the tree and hole in my roof with a tarp to prevent rain from doing further damage. Then I needed to do serious tree removal throughout the whole property including the roof, but as soon as that was done, I called Steve Totilo the owner and within 3 days he had a crew working on the repairs and reshingling which were done in short order. The work looks impeccable and I would never hesitate to recommend him for any outside home repair or painting you might need.