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I've been watching videos by Scott Burdick, Morgan Weistling and others.
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Are these the ones you get from that rental place, Jeff?
Painting over dry paint is easy if you oil out the dry surface first. Otherwise I find the drag of the old paint on the new stuff is not pleasant and it's very hard to match colors and values. (I oil out with a 50/50 mixture of linseed and mineral spirits, brushing it over a dry area and wiping most of it off. It restores the true value and color to the dark areas and makes a nice surface to paint into.) The old paint has to be very dry or it will smear during the oiling out, though.
I think it would be just about impossible to paint everything perfectly in one go, so using multiple layers is pretty much essential.