There's a glitch with duplicate bills, it might have to do with data not resetting properly with the "reset progress" option or a game over.
I played a bit the first time until I got caught and lost a lot of money, so I reset progress and started a new game. In that game I received a new set of emails on day 4 and a new bill to pay due day 8 or something. When I hit day 6 I paid the bill closest to expiring, but the other bill was paid, so I got a game over next day. Then, upon starting a new game, I had 3 sets of emails, and I got a second bill due tomorrow.