Regarding the course upload - have you been able to use the same CSV successfully in the browser tool?
You already mentioned the LDAP authentication method, so I would almost assume that you looked into the equivalent Enrollment plugin, but in case you have not: https://docs.moodle.org/38/en/LDAP_enrolment
You could also look into the Moosh (MOOdle SHell) command line tool. Seems like it may work decently on Windows.
You already mentioned the LDAP authentication method, so I would almost assume that you looked into the equivalent Enrollment plugin, but in case you have not: https://docs.moodle.org/38/en/LDAP_enrolment
You could also look into the Moosh (MOOdle SHell) command line tool. Seems like it may work decently on Windows.
Not sure if any of that gets you closer to your desired workflow, but I hope it is useful, nonetheless!