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So do I, for as often as possible. If I can't get that upgrade done, either I take it to (an unauthorized) repair tech good with Macs, or I fire up an older Windows tablet or laptop I have after I make sure it is OK. I go with option 2.

Dealing with OS is always a pain in the ass.

Operating systems: you can't beat them, and you can't kill them. That tablet I took out is still charging; it will take a while, then I'll see how well the thing works.