You should lightly sand, then prime it. You don't suck at DIY, you are doing great! The hardest part is realizing that you can do anything you set your mind to.
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A lot of people prefer the look and durability of oil. You should NOT paint latex over oil as it tends to peel. If painting water base enamel over oil base trim or wall as well, need to primer first. Same with kitchen or bathroom.
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