Is it okay to steal from the guards (ex.bruma guards, imperial legion guards, cheydinhal guards, etc.)? cuz i dont want to have a bad glitch halfway throughout the game...

yea but i dont know why you would. they usally dont have anything good.

Just for fun, I went into oblivion and started pick-pocketing instead of killing. (I was 100% invisible). I was actually able to pick-pocket a dremora about 5 times (the stuff kept coming back) before it stopped.

steal from town, have cops chase after you
head to mazogas hut, wait inside

mazoga will kill guards for you and you take all of the guards stuff

the only reason that i would even think about pickpocketing the guards is so i can have their town armors

You can't pickpocket their armor, you need to kill them.

i pickpocket them when their sleeping so they arent wearing their armor...you can only pickpocket items that are not equiped and when they sleep they have on no armor besides like gauntlets and maybe boots...never cuirasses

you can just go to one of the guard houses and do it

Didn't know that, sounds much easier.

Cheers.