I'm having a hard time with these when strumming chords
they seem to catch on the strings at certain places or just sound completely different than a down stroke and weird too

any tricks to upstrokes?
rotate your wrist. when you strum downward, the outside of your wrist kind of points out and away from you. when strumming upward, try moving the outside of your wrist more toward the direction of your body. It helps to not be soo stiff either. Unless your palm muting, loosen it up on chords.
When you refer to those wrist positions, am I supposed to like rotate them during the strum, or keep them in that position all the way down (And then up)

Like is the strum about twisting the wrist, or moving the arm up and down respectively
keep them in that position. so lets say you play an open G chord. On the downstroke, your wrist faces down. and on the upstroke of that G, your wrist kind of faces you. Just play however is most comfortable for you. Practice more and you'll get the hang of it.
think of it like a zipper on a jacket. the downstroke is like when you unzip your jacket and an upstroke is like you zip up your jacket.
^weird but good analogy.

is the problem actually with the sound itself or does your hand just not feel able to be able to do that, so you get a different sound with it?
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it's like the pick will catch on the strings as opposed to gliding along smoothly like with a down stroke