Automatic Scheduling issue

As far as I am aware, it will set it on the date itself as in the time you click save changes. Once that has been run, then the next time will be two weeks.

?

Please clarify.

When you click save changes, it will show the date that you saved (which is correct). That will trigger the scheduler. Once the scheduler runs, it should reflect the date of the next run. If for some reason your scheduler is not running, you can trigger it manually using WP-Crontrol plugin.

Also I recommend using a real cron https://support.hostgator.com/articles/specialized-help/technical/wordpress/how-to-replace-wordpress-cron-with-a-real-cron-job