With older imacs, is there a point when you SHOULDN'T upgrade to latest OS?

I may have worded that poorly but basically what I'm after is this: I know Apple lists the compatible Macs going back X number of years with each OS update, but is there a point where one is better off staying put with say Mountain Lion on iMac 21.5 Late 2009 (12GB RAM) vs. updating to Mavericks and eventually Yosemite.  Obviously, the newer the machine the better apt it is to take advantage of the newer OS, however will taking on latest OS actually slow down an old Mac?  Is this making any sense?

I disagree. My 2009 MacBook ran Mavericks very well. Better, gasp, than Snow Leopard.
Mavericks is designed to be more efficient than previous OSes and should run well on the hardware that Apple says will support it.
If you're alrady running Mavericks, I wouldn't downgrade. As you guess, you'll have problems with existing apps you've installed that may not work with 10.6. Not to mention the lack of security updates. You'll be exposing yourself to all sorts of known vulnerabilities by downgrading.
Stay are you are. You might not see the value in upgrading to Yosemite, but I wouldn't backtrack now.

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