Thanks for this investigation! This issue has been discussed in multiple
places, like here where a udev rule is recommended:
https://github.com/systemd/systemd/issues/2891

I wonder if we could downgrade the "Requires=sys-subsystem-net-devices-
XXX.device" to a "Wants=sys-subsystem-net-devices-XXX.device" and add an
additional triggering condition on the sysfs path
("ConditionPathExists=|/sys/subsystem/net/devices/XXX"). AFAIU this way
the wpa_supplicant unit should fail immediately, if the devices (& its
sysfs path) is not there but start as soon as the dongle is plugged in.

https://systemd.network/systemd.unit.html#Conditions%20and%20Asserts

I guess this needs some experimentation to fully understand the side-
effects.

** Bug watch added: github.com/systemd/systemd/issues #2891
   https://github.com/systemd/systemd/issues/2891

** Changed in: netplan.io (Ubuntu)
       Status: Confirmed => Triaged

** Changed in: netplan.io (Ubuntu)
   Importance: Undecided => High

** Tags added: jj-rls-incoming

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https://bugs.launchpad.net/bugs/1906646

Title:
  Timed out waiting for device /subsystem/net/devices/wlan0

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