As nice as a Mac is for a lot of things, using any single OS will tend to lock you in and keep you from using better tools that are available on other platforms. So, although it still isn't exactly clear *what* organization you specifically need done, I'd say: 1. Immediately export *all* your images from Photos. Figure out the best way to sort/triage them that is open to everyone. 2. Eliminate the PDF conversion step. Find software that does OCR directly on the source images. 3. Consider using a crowdsourcing platform to do some of the easy-ish-for-humans tasks. [Zooniverse](https://www.zooniverse.org/projects) is one that I came across recently. You can turn 44 years into months if enough people find the project interesting. 4. Once you amass enough text/annotations, *then* consider if it is best managed by an off-the-shelf indexing app or if you have to build some custom, database-backed software. 6fae61b8451a78ca78d77fe0588ac455e86217023178dfb7db5e88620f02c208