I considered deleting the post, but this seems more cowardly than just admitting I was wrong. But TIL something!
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Fair, but there's also a lot of businesses that don't accept $100 bills which would make paying for smaller everyday things annoying, and realistically I don't think any car dealership would want to deal with 2,750 $100 bills either. Besides, with infinite money you could hire people to count and move the money for you, if it's $1 bills instead of $100 bills you simply hire 100 times as many people!
I think it would be easier to go to thebank now and then to exchange some of your $100 for lower value bills than to do the opposite.
Besides, if there are places that don't take bills less than $20, there are a lot of places that aren't going to let you pay with only $1 bills. I can't imagine a car dealership letting you do that. Or if you want to buy a home, etc.