I've tested my tools pretty extensively across Windows and Linux in H20.5, 20.0, 19.5, and 19.0 so I'm a bit surprised that moving to a version with the same python version is causing problems.
So it looks like 21.0 now comes bundled with FontTools 4.55.4, which is older than what I've been developing with. One of the errors were caused by issues that were fixed in a later release of fontTools (4.59.0), but the other issue appears to be an actual problem with the version included since it doesn't occur in 20.5 even with the same exact version of FontTools installed