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Comment by WalterGR | Hacker News Reader

     buy Windows 10 Pro for $164 but it will break compatibility with their Office Software

How so?

Office 2003 and under won't run on Windows 10, they'd have to buy a new copy of Office. It won't work on 8.1 so 10 is out of the question:

It actually does work, though not officially supported and there is no way to get the Office Assistant working properly for example.

That sounds more like an added feature than a problem.

It's 12 years old! Isn't it reasonable that support is phased out?