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I thought the darks were not popping enough, thus the raw umber is not grayed down.
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If you are going to do layer on top of this, save the dark accents for later. If you do not plan to go farther, dark accents are OK here.
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...what the drying time should be in between steps?
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If you paint in layers, each layer should be dry before you add the next. If you are using the direct method, you can paint wet into wet. Just to confuse you more, you can combine these methods if you wish.
But just remember, you cannot glaze onto a wet surface or you will mess it up.
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When you want the paint to be "buttery" do I need to add any medium to the oil or just put the paint on thick and smooth?
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If you are a patient person you can avoid the medium. If you're like me, you'll want to use something to make it dry overnight, i.e., Liquin, Galkyd Lite, etc. Don't ever use turpentine as a medium. Turpentine is for cleaning your brushes.