Howdy! I'm the author of PhotoStructure. I initially wrote it to organize the boxes and boxes of old hard drives from the last 25 years of photos and videos th

Howdy! I'm the author of PhotoStructure. I initially wrote it to organize the boxes and boxes of old hard drives from the last 25 years of photos and videos that my family and I have taken. PhotoStructure libraries are uniquely cross-platform and cross-machine, so you can import on your old windows box, sweep all the non-bitrotted files onto an external drive, take the drive to your Mac, run it there, and get a single, comprehensive directory with all your stuff. If you have a NAS, it's even easier: PhotoStructure supports libraries stored on remote filesystems, and it also runs in docker. Currently I delegate the uploading task to external applications, like syncthing or Resilio Sync. Making everything automatic works well for my family, but may not be what you're looking for. Note that I've open-sourced several components of PhotoStructure, but the application itself is commercial software. There are free and paid plans available. https://photostructure.com/faq/why-photostructure/ https://photostructure.com/faq/why-photostructure/