“You keep saying its a one time thing for as long as Microsoft supports it. What’s the chances of them NOT supporting it? What does that really mean?”
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In my experience, they will support it for many years (usually longer than you'd want to use a computer / laptop, about 7 years). Then, you'd need to upgrade. To be honest, at that time I'd recommend a full new system because the processor will be too slow for modern applications.
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