re: Can I just say, Apple users frustrate the heck out of me?

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The real problem is how simple the vast majority of tech stuff really is (what file formats exist and how can they be converted ? What is an IP address? What is an operating system?) and how totally inept + disinterested the average person is as to how anything works.

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Right. Some people think the general pop is more tech-savvy than 20 or 30 years ago, but I think the opposite. Most people can use tech, but that's because so much dev effort is poured into UI/UX which hides what goes on under the hood. There are plenty of people who sit in front of a computer for 8 hours a day every single day but basic file management is some dark art.

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So I decided to “next level” the project and help harvest/sort photos on a Synology drive (I would make a share per person, then dump each person’s folder into a share in a plex server which would be able to play from each person individually or in aggregate). I gave up before I started, because Plex doesn’t support HEIC, and I’m not dealing with asking people to convert files or going through the process of converting them for them because it just becomes a hassle (and in this case a never-ending one)

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Don't know if there's a way to do it on a synology, but you could host the files on something else and script the conversions. I know it's not quite as plug and play, but it's do-able without hassling everyone else.