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Certain surfaces, when house painting, should always be primed before paint is applied, for example, bare wood and shiny surfaces. Two coats of material over primed areas creates professional results by building layers of paint. Laminating layers of paint over pre-painted surfaces helps to create lasting, durable finishes. Multiple layers of paint will also have a better feel to the touch.
Yes, when it comes to your home, interior or exterior, more expensive high quality paints will provide better workability, a more professional look and a longer lasting beautiful finish. Higher quality paints provide better wash ability and resistance to scuffing.
A possible exception to using higher quality paints when house painting, could be the repaints of rental properties with frequent turn over and abuse.
This actually depends on the type of siding being painted. As a house painting contractor here in Eugene, I have discovered smooth lap siding looks more professional without back brushing. Also, HardiePlank does quite well without back brushing. The different varieties of T-1-11 however, with its rough surfaces, finish much better with back rolling by working the paint into the nooks and crannies creating a consistent finish.