Chozo

A big part of the reason is that $100 notes are rarely handled by most people, even among cashiers. So the recipient of the counterfeit is less likely going to be familiar with the designs on the bill, and less able to identify imperfections. Cashiers handle hundreds of $20 bills every day, but might get a $100 bill once every six months (if ever) depending on where they work.

Another big part of the reason is that if you manage to break a counterfeit $100 bill for a $10 purchase, you’re going to get $90 in real money back from the cashier. This is the main point of counterfeiting for most people; to turn the fake money into real change from purchases. You don’t just want to buy your weekly groceries with the counterfeit, you want to “buy” something and get free money out of it. So a $100 bill helps to min/max that process, while offering a lot of flexibility in where and how you choose to “spend” it.

Is he inserting nightmares directly into Jon Stewart’s sleeping face?

Usually early February, as my employers generally wait until the latest allowed day (Jan 31) to actually process/mail my documents.