Not sure if this will still help @PokeParadox, but just in case someone stumbles upon this thread:
After reading a little bit more about chrooting modern GNU/Linux systems, I've come to the conclusion that systemd-based distributions are not very well suited for running in a traditional Unix Chroot by first principles of systemd. Although my Debian 10 was in fact doing everything I needed, I thus decided to migrate to Devuan 3 (beowulf), a distribution derived from (and almost identical to) Debian 10, but not depending on systemd.
As a result, my system feels much more solid now: In