Is it proactive? For example:
- Length of time since last key event
- Amount of data
- Previously determined OS attempt
Or is it reactive?
- Due to performance?
- Perceived slowness?
- Hardware failure?
However, what if it's a server? How often do you rebuild things, even just the OS? Yes, I know up-time is king. I do.
However, if you can unlock more efficiencies through an OS upgrade, why don't you? Why not be proactive?