We have had a mixture and the ones who are strict are usually the ones handing out marks or deducting points and have the oddest request.
I asked one teacher at BTS Night, did we really need blue eraseable pens? I said my DS is a lefty and his hands are covered in blue by the end of the day. She looked at me like I had 3 heads and said of course it is necessary it is what I require. She said maybe my DS had a problem writing

And bc I was annoyed I said and we have to have blue...she said yes no black...are you kidding me? Well I did find blue erasbale pens, got the last package at CVS, tons of black available, some kids did not and they wound up with calendar marks(like a demerit).
And last year DS had a wacky priest in HS that was very specific about things he wanted in class and took off homework points for it. This is a Catholic school and it is theology class but he required certain colors and certain types of notebooks. The oddest request was not school supply related but a request for a certain type of Christmas cards so the boys could send them to the nuns in a nursing home...ok nice gesture...except they had to say Happy or Blessed Christmas on them, not Merry, and they had to be blank inside, and he only needed 3 of them. At first I did not think this request would be a big deal, we had two days to get them. Well after the 5th store, we found some with Mary and Baby Jesus on the front, and it wished them Blessed Christmas on the inside very small so there was plenty of space to write a message. He was scared to show them to Fr Thom....Fr Thom looked at them and said they did not meet the requirements....DS said Father we went to 5 stores and he rattled them off, even a Hallmark store. Finally the priest said they were fine but he was disappointed that they were not exactly what he specified. It was a box of 16 cards, boys were offering big bucks for cards bc their parents could not find any acceptable either. DS just gave them the cards.
MOST teachers are great and very accommodating but there are a few that ask for that odd size lined index cards that can not be found anywhere, and even if I ordered it online I would have to order a case