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iMac "Core 2 Duo" 2.66 20" - ideal version of OS X?

With some difficulty, I was able to get OS X 10.6.8 installed on my iMac model referenced in the subject line. I usually prefer running the latest and greatest version of anything on my machines in order to have as many security patches installed as possible. In the case of OS X, I understand running the latest and greatest comes with trade offs, namely performance and compatibility. Many years have passed since this iMac release and I'm sure there have been many thoughts about how far this machine should be upgraded.

My machine has 8GB of RAM and a 320GB hard drive. I understand that it will be almost impossible to get this connecting to modern websites and that is not my intent here. Rather, I want to use this machine as a bridge to my collection of older 68k and PPC machines. Along the way, I want to use this machine to explore older versions of productivity software, games, and older versions of Python.

I would like to tap into the collective wisdom of the community here and ask for opinions and thoughts on whether I should stay at 10.6.8 or upgrade to a higher version. This will be a machine frozen in time. The question is what is the best time?

Thanks! 🙂
 
I think Snow Leopard is spot on for that CPU. You've got access to a ton of earlier PPC software with Rosetta plus the later Intel software. Snow Leopard is also very perky with those machine specs so it's a pleasure to use.

I've run 10.11 El Capitan on a Mini with similar specs and it's still very nice to use, but if you upgrade past 10.6 you'll lose Rosetta and PPC backwards compatibility.
 
If you want to be able to run PPC binaries with Rosetta, stick to Snow Leopard. I've got nothing against Leopard (I wrote bits of it) but SNL is superior.

https://en.wikipedia.org/wiki/IMac_(Intel-based)#3rd_generation:_Unibody is useful.

That's quite a capable machine (iMac9,1 with Penryn processor) and you do have other options if you're adventurous. By default, Snow Leopard runs the 32-bit kernel -- you can boot into the 64-bit kernel for some extra performance but some drivers may be missing or iffy. Or you could use the OpenCore Legacy Patcher to be able to run up to Sequoia!

IMHO, if you want the best network bridge to 68k and PPC for the money, get a Raspberry Pi and install netatalk-2.x.
 
Reckon the sweet spot will be Snow Leopard for performance and PPC compatibility, the only website you probably want is Macintosh Garden to download apps and games. RAM is super cheap, along with an SSD which will really give it a kick along.
 
With that era of C2D machines, I tend to run both Snow Leopard and El Cap. For a long time, I was using El Cap more, but now it's far enough out of support that it is starting to break in the same ways Snow Leopard is broken -- so I tend to boot into Snow Leopard more now, and work on fixing the issues instead of using a slower but more capable OS.

SL gives you a good trade-off between speed and compatibility. There's quite a bit of stuff that's been backported to work on it, and more people are starting to turn to it as a "good x86-64 platform" reference now that Apple has fully indicated its shift to AARCH64.

Hopefully, this means that we get an icebrew similar to tigerbrew that continues to support the platform now that homebrew has left it far behind.
 
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