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How low maintenance can a small home setup be?
(alien.top)
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Let me check my crystal ball... hmm yes, maybe.
Maybe you should consider putting a simple to use "OS" like /r/CosmosServer or CasaOS on that little server, so even he could do basic things with it like update a container. But also make sure you have a reliable remote option over SSH for example.
Nothing is 100% foolproof.
Yes, I have no doubt it could be tricky, maybe not even possible at all. However it could maybe be doable with the correct setup.