Windows Timed Automation Script -- 2

The goal is simple: on a single Windows machine I want a lightweight script that can launch my own custom software at a specific start time, feed it a handful of files according to time-based rules I define, and then close the software cleanly at the shutdown time I set.

Here is what I need the finished solution to handle:

• At boot or via Task Scheduler, wait until the scheduled start time and open the custom EXE.
• While the program is running, pick up a series of files and run them only when their individual time triggers come due.
• After the final file finishes—or at a hard stop time—close the application and exit without user intervention.
• All timings (start, per-file triggers, and stop) must be editable from a single place such as a JSON, INI, or simple text config so I can maintain it myself.
• Clear logging of each action so I can audit when the program opened, which file ran, and when it shut down.

I’m fine with PowerShell, AutoHotkey, Python (with pywin32), or a compiled executable—whatever you feel is most stable on Windows 10/11—as long as it runs without extra installs beyond what the OS already provides.

Deliverables:
1. The script or compiled tool with commented source.
2. A brief README showing how to adjust the schedule, add/remove files, and set it up in Task Scheduler.
3. Quick hand-off session or short video demonstrating it in action.

If this sounds straightforward for you, let me know how you plan to approach the time-based triggers and which language you’d prefer to use.