The first thing that you want to check is how many plugs are already on the circuit as well as you will want to tie into the existing circuit with the same size wire example 12/2 to 12/2 so you do not creat a fire hazard.
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Personally I think it is better to paint the trim while it is on the wall that way you can sand joint and do prep work to make the material look better. It is a good Idea to paint it with a sandable primer first.