Thanks for checking. I did some more testing and I think I found the
actual issue.

When I run systemd-networkd-wait-online without arguments, it times out:

$ /usr/lib/systemd/systemd-networkd-wait-online --timeout=10
Timeout occurred while waiting for network connectivity.

But when I specify the interface, it works:
$ /usr/lib/systemd/systemd-networkd-wait-online -i enp3s0:degraded --timeout=10
(succeeds immediately)

I noticed that apt-helper wait-online appears to call
/lib/systemd/systemd-networkd-wait-online directly (based on strings
output). My guess is that it's calling without interface arguments,
which would cause it to wait for all interfaces, including my
unconfigured wifi interface (wlp2s0) that's stuck in "configuring"
state.

The netplan-generated drop-in for the systemd service has the right
arguments (-i enp3s0:degraded), but that only helps if something uses
the service rather than calling the binary directly.

Does this sound right? Or am I misunderstanding how apt-helper wait-
online is supposed to work?

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https://bugs.launchpad.net/bugs/2151846

Title:
  netplan generator creates invalid systemd-networkd-wait-online syntax
  causing apt-daily timeouts

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