How do I react to external program launch inside an Automator workflow?

Question

As per the title, I need to automate unwinding my date 7 days back upon I launch a specific macOS application bundle and putting the timestamp back to normal 45 seconds into its uptime.

What I need to do is:

1. Watch an application bundle with a specific name to be opened (like FileSystemWatcher in .NET)
2. Change the date 7 days back between the Application opened by user and First application window appears events (events written in pseudocode)
3. Wait 40-45 seconds while the application checks the trial period status
4. Wind the date forward to normal state.

It looks like the Automator standard library does not implement a wholly native solution for this part of workflow, and I need to find a workaround. I know it is wrong using non-seamless methods of application integration, like launcher shell scripts, and I do not prefer cracks either, just because they are illegal and also due to the fact of putting a stamp into the application menus, like K'ed by MacKed team. This severely damages the eye candy and is too explicit saying the software has indeed been pirated.

I do not endorse nor condone any forms of computer piracy. This question has been asked exclusively for educational purposes.