If you were starting from zero, how would you handle how accurate OCR is for older paper boarding passes?

I want to digitize them without manually entering every flight number and airport code. is exactly the right target. The best systems are the ones you will still use after ten trips, not just one enthusiastic weekend.

Some of the paper is wrinkled and the ink is not great anymore. 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.