Edit - First, thank you for any replies and to anyone who read my original post. I am learning this with the FSM and two repair manuals. I used a second set of eyes to go out and triple-check that I hadn't made a bunch of mistakes. The first cylinder gets a compression reading on the gauge at about the 45 mark (if it existed). When bringing the pulley mark to zero with the help from my second eyes, I get a completely different and much less dramatic looking scenario.
The timing mark on the chain is a V (sitting at 2) versus a shiny which I couldn't find before. This looks less problematic than the crazy scenario I originally posted about but is still puzzling to me as the PO's mechanic didn't work on the timing but said there was a definite issue. Do these markings look off to you?