two ortho/para directors on ring, which takes precedence?

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ifonlyifonly

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CH3 bigger than OH

This. Not only is OH smaller than CH3, the O is also more electron-rich, which means it's a stronger activator of the ring as it donates those e-. The electrophile, being electropositive, will tend to go ortho moreso than para by just a little when you have a strong activator IIRC.
 
Is electrophilic aromatic substitution even part of MCAT content topics for orgo?

It was removed nearly ten years ago, yet some people still ask questions about it in the Q&A section. I'm not sure why, but if they want to waste some of their study time preparing for topics not tested, it's their choice.
 
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