re: iMac 5K
First and foremost:
RULE: wait 6 months before even considering “upgrading” to the latest macOS.
Apple has a dismal track record with new macOS releases, introducing many bugs, including severe security bugs. Rarely if ever are new features relating to getting work done efficiently the focus; almost always such facilities are degraded. Add-in compatibility problems and anyone using their Mac for getting work done has everything to lose, and likely nothing to gain.
If you have an existing Mac, what then? Things have settled out into a pretty simple situation:
- If the Mac is on macOS Mojave or earlier, stick with what you have, barring a compelling reason. You don’t need need new headaches. Troublesome exceptions to this rule are driven by software changes, such as Adobe no longer actively updating Photoshop for macOS Mojave, which is now ~4 years old.
- If the mac is on macOS Big Sur or macOS Catalina, you are almost certainly better off on macOS Monterey at this point. But check your software to be sure—32-bit applications do not work on Monterey. While macOS Monterey is not problem-free, but it is more stable than its two predecessors, which never had all the bugs worked out.
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