It's not that it hasn't gotten better, but that the entire infrastructure that's underpinning the GUI is simply completely different than what people are used to. And I'm not just talking CLI here, because the average Windows user likely doesn't use that to begin with – it's things like filesystem organization, software management, driver installation, configuration files, etc.
And it's not that these barriers are insurmountable either, but they DO require a significant amount of cognitive effort that not everyone is willing to put in.
I’m sure there are many ways to improve on this solution, but they would all require significantly more effort (ElasticSearch isn’t exactly trivial to set up).
This is really just a proof of concept, the most minimal viable implementation that gets you something similar in terms of functionality.
For instance, Windows Recall stores OCR content tagged by app, this solution doesn’t. Also, as others have mentioned, a practical implementation should likely check if anything has changed at all and discard any screenshots that don’t have any new data.