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I haven't played around with pixlr, so I'm not sure how much control you have over things.
As far as the cap logo goes, the stock one that OOTP comes with is a 150x150 pixel PNG file with transparency where there is no artwork. Presumably, OOTP will scale that appropriately for the cap logo.
Personally, I prefer to work with a cap template that lets me generate the entire cap. When doing that, I find that the cap log shouldn't be much more than 50px high, although extremely wide logos generally look better if they're not quite as tall.
Also, I recognize (well, I made) that font, and I suggest you don't try mixing upper and lower case. The font (and most of the MLB fonts I made back in the day are like this) is kind of two-in-one - the upper-case letters are a plain block font that you'd generally see a player's last name rendered in, the lower-case letters are the team-specific font.
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