Semi-gloss over flat painted wall?

Can you put a semi gloss interior paint over a wall that was painted with a flat paint? I am painting one of the bedrooms in my house with Valspar Signature semi gloss finish paint. What I am getting is spotting or something you can see the roller marks on

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Chair rail and molding color.

Painting dining room a soft gray above chair rail and white below. Should the chair rail and crown molding be white or a nice darker shade of the gray? We are having a real dilemma.

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