Ok, for anyone running into the same problem: it was 2 separate issues.
1. Error 127: Even though I was picking it directly through the computer's file browser, the Wwise-Unreal integration settings somehow still had the wrong filepath. I manually copied it (you can get that by right-clicking on a file, then holding down alt and clicking "Copy [FileName] As Pathname") and pasted it into the little field for it in settings. Problem solved.
2. Only getting one SoundBank when trying to Generate Sound Data: Not sure what was going on here, but I had to manually create a Soundbank (with the exact same name as the one already in Wwise) via Unreal's Content Browser, drag the events from the sidebar into another Events folder, and then add the Events to the Soundbank. My collaborator also had this problem, so looks like it might be a bit of a widespread bug? Dunno.
Wwise Version: Wwise 2021.1.2.7629
Unreal Version: 4.25.4
Hope that this solved your problem if anyone else comes across this!