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So I'm working in a small company that has a few employees, we have lots of images, photoshop documents, and illustrator files.   All of which need some sort of tags to make things easily searchable, and make it easy to collaborate.  We use Mac's and PC's.   I haven't seen any Digital Asset Managers I like, and I don't want to place my bets on a software company that goes broke, so I'd rather just use Sync and built in OS file explorers.  I plan on using the Mac's and Finder as the main way to access, organize and tag files.   I know windows cannot see macOS tags, but does windows pass along tags, and would Sync properly pass these along?  So if a file is synced from a mac to a PC, then back to a mac again, would the tags be retained? 

Is this a crazy way to do things or should I just find a proper Asset Manager?

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Windows does sync the xattrs. Are you going to sync files to some  non-local drive? We've earlier discovered interesting cases with syncing to/from a host linux drive mapped to Windows's VM, drive pools aggregated using different special s/w, etc, where writing xattrs and streams was a bit complex.

Here you can read some info about this all

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