Mystery #2 solved. Somehow, a Raspi on the network has started showing up with two different IP addresses – so what I thought was the new pi isn't. I figured this out after making a second SD card, which also didn't recognize the "default password" as it's not the address I thought it was. Feeling stupid about this.
Mystery #1 still remains. Files added with one computer "don't stick" while doing the exact same procedure on the second works as expected. This caused much frustration and wasted time, and weirdly, when I got the card correctly written is when the second IP address showed up for the other pi.