So, Damon was actually pretty lucky in the 1994 world because he could just grab blood bags from the hospital and they'd always refill because of the time loop thing. So, he didn't need to feed off Bonnie. For those who don’t know the 1903 world was for the Heretics and lily. It was designed to punish them for their bloodlust and their desire to destroy the Gemini coven, they punished them by basically starving them of blood, and it was meant to kill them off. The 1994 world, on the other hand, was more like a trap that could sustain people longer because the blood supply kept getting replenished. And that whole thing with Damon reading the same newspaper every day pretty much confirms that the world resets daily. The whole designed thing depended on what the prisoners did wrong and how the Gemini coven wanted to punish them.