[mceachen]

May I ask, how are you saving the tags? Are you writing to sidecars?

Be careful with overwriting your originals. Many years ago I used jpegtran to rotate losslessly, but didn't realize it was removing all the metadata as well.

I added a bunch of heuristics to PhotoStructure to infer missing tags based on sibling files, specifically because I'd borked so many of my own photos.

FWIW, I've tried to make design decisions that will hopefully allow libraries to be very long-lived. PhotoStructure can copy unique (by SHA) originals into a dated subdirectory, and has what may be the most advanced duplicate image detection around (just added in the newest version). Your library is cross-platform (for example, stored on your NAS, created on your mac, then opened on your Windows box, and everything just works). The sqlite database is a straightforward schema.

[jdmcnugent]

I just put the tags in the file name, like “2019-12-25_xmas_bob_grandma.jpg”. Obviously you can’t go crazy with a bunch of tags, but I think I can get by with 2 or 3 tags at most. I was afraid to use sidecar info or xattr because I think that data can be lost if the files get moved between file systems (ie eventually moved from the current hdd to the nas I have yet to buy, etc). I definitely kept my raw unorganized folder on the ext hdd for now, but I’ve run several scripts to make sure I didn’t inadvertently overwrite or miss anything.