Having the ability to identify an ETA against each Flight Record (synchronized with local time) which generates a 'Past ETA' Air Maestro notification/email to specific personnel and a text notification if ETA is exceeded by 'xx' minutes would provide a basic form of Flight Following.
Having a 'landed' checkbox or 'landing time' could be used to override this notification once the aircraft had landed.
This should ideally speak to the Scheduler as well, so it may be worth considering a function that allows submission of a Flight Record to update a scheduled task.