I’ve never had to use a bill larger than a $50. Used twenties plenty of times and never been asked anything.
The only complaint I have when you do use larger bills is that expect your change to be all ones.
After using a fifty you kinda feel like it’s time to go to a strip club.
Back in the 70's my wife was in a hospital in Miami having our 3rd child.
I went to the hospital to visit and was taken aback when I found I had to pay to park in the hospital parking lot.
Being the smartass I am, I gave the toll booth taker a 20 dollar bill.
He gave me my change in...Quarters. I lose !