Can you confirm that you have wpasupplicant 2.1-0ubuntu7 ? I. e. you should see
$ systemctl cat wpa_supplicant.service |grep Before Before=network.target
Your journal looks like it would stop wpa_supplicant before network.target.
Can you confirm that you have wpasupplicant 2.1-0ubuntu7 ? I. e. you should see
$ systemctl cat wpa_supplicant. service |grep Before network. target
Before=
Your journal looks like it would stop wpa_supplicant before network.target.