One irritating job is enough
You can begin with a file list, a weekly check or a shortcut you press yourself. Notice which part repeats, then make that part easier to inspect or perform. A small script or an existing rule may solve the whole problem. There is no requirement to introduce another platform.
Try a preview first
The task guide includes a Python example that reads proposed filenames and prints a plan without changing files. It gives you a concrete input, useful output and awkward cases to test. The same preview-first approach can work for checklist preparation, folder organisation and other routine jobs.
Decide what improvement means
For workplace admin, include checking and maintenance when estimating time saved. For a personal project, learning a technique or making a control easier to use may be the point. State that goal plainly, keep the manual route available and judge the experiment against the job you actually wanted to improve.