As noted by Key Turner in the forums there are some non-ideal scenarios with the way that we currently parse passwords and the (somewhat arbitrary/adhoc) rules that we apply.
The suggestion is that we leverage the cracklib library to check the password. There is a python module packaged in Debian which we could leverage within inithooks. We may still need to do our own password checking in some scenarios (some apps have their own password complexity checks and we'd need to match them) but generally I think we could run with cracklib checks.