"Also, what is the best way to know if a group is donating/withdrawing instead of memorizing them all?"
An easy way to think about this is, if there is an electrophile on the benzylic position it is ewd. Alkyl groups a weakly activatiing, if there is an atom that has lone pairs on the benzylic position but also particapates in resonace (not to the aromatic) is moderately activating and if there is an atom with lone pairs that is not participating in resonance (outside of the aromatic) then it is strongly activating.
Phenol is the strongest activator. If you an amide with a nitrogen substituent that is a phenyl then its moderately activating and like I said Alkyl groups are weakly donating. What you really need resonance structures for are the halogens. They are electron withdrawing but because they have more resonance structures for the ortho/para positions they are ortho/para directors.
Oh yeah and if there is an atom with a full blown + charge then its strongly deactivating.
You shouldn't just memorize things to memorize them, if you memorize something it should be because you looked at it that much and it just so happened to stick to your memory. Really, just understand how it works and you'll be fine.