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Very interesting. 

Does itch / playdate have an API way to log in (or are credentials stored on the user's machine?). Presumably this would work on raspberry Pi? (PiOS = Debian). 

Might be nice to have a feature that just flags updates, rather than actually doing the uploading to Panic's servers?

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Itch has a key based API that this uses, and Playdate has no API, so it needs to use username/password to log in.  I currently have it set to use a json config file which you put in your ~/.llpdmgr directory, which can be set read only.  Once an api is available for Sideload, I'll use that.. but for now this is all we have. :( 

Yes, it should, It's Electron/Nodejs so if you can run other Electron apps (eg Discord), you'll be fine.

And yes, it will only upload new/changed files.  I will eventually add options to only show updated items, or auto-update, etc...

Looks really useful!