I think it would be more interesting to pick a card with a vibrant, detailed background (e.g., N162). If you went the portrait route, I would definitely get it from someone who specializes in realistic portraits. The Cy Young and Walter Johnson tattoos someone posted are not accurate representations of the players. The artist could, if you wanted, reference some real photos of the subject to add in details that the card didn't capture too. Another idea would be the trade card route since the facial details don't need to be spot on and they tend to have more colors (e.g., Tobin lithographs). A new school tattoo artist could produce an awesome version of a Tobin lithograph if you are looking for something that is inspired by the card rather than a copy of it.
Best of luck with whatever you decide and post some pictures when it is complete.
p.s. Since we are on the subject of tattoos, I have to post a picture of this one that I just got on Tuesday.
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