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Constant maintenance? What's that?
Here's my setup:
I honestly don't think about it. I run updates when I get to it (every month or so), and I'll do an OS upgrade a little while after a new release is available (every couple years?). Software gets updated periodically if I'm bored and avoiding more important things. And I upgrade one thing at a time, so I don't end up with everything breaking at once. BTRFS snapshots means I can always roll back if I break something.
I don't even know what TrueCharts is. Maybe that's your issue?