My boarding pass history is split between file types and platforms.
I want one system that stays searchable years later.
Naming everything manually sounds fragile and annoying.
I want one system that stays searchable years later. is exactly the right target. The best systems are the ones you will still use after ten trips, not just one enthusiastic weekend.
Naming everything manually sounds fragile and annoying. is the part most advice ignores, and it usually ends up being the reason people quit a tool or workflow.
I try to keep it simple: solve the biggest pain point first, then add extra optimization only if I keep up with it naturally.
My rule is that if a setup takes too much manual maintenance, I replace it with something simpler even if the theoretical upside is lower.
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