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One tip that I have seen in numerous posts is that upgrading Leopard to Snow Leopard from any version less than 10.5.8 has reported more issues than those who do. It may be nothing, but, all in all you should be keeping your system up to date anyway.
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Program Compatibility
So far any of the applications that I used on my late 2008 Mac Pro have been working just fine. Many popular programs such as Growl have not yet updated for Snow Leopard but so far appear to be working just fine. Those programs Control Panel entries will cause it to restart into 32bit mode before launching, which is mildly annoying.
Possible Issues
I have been reading that in some cases Mac's which are capable of using the 64bit kernel are booting into the 32bit kernel. The easiest way to find out if you're capable is to drop to a prompt and paste in:
ioreg -l -p IODeviceTree | grep firmware-abi
If you are 64bit ready then you will see the following, if not then you are booted into 32big mode:
"firmware-abi" = <"EFI64">
Check out this page on 9to5 Mac for information on if you are 64bit capable and what to do about if you're for some reason booting into 32bit mode: click here.
Personally I do not think it is a terribly big deal, for most people, if you are not using the 64bit kernel.
Overall opinion
All in all "Snow Leopard" does exactly what it was supposed to do, improve and optimize your leopard experience. It was in my opinion a rather bold move to forgo the typical fancy, shiny new (and possibly useless) features that so many of us expect from an upgrade. This does, however, set the bar pretty high for 10.7 which people are going to expect to be a huge upgrade.
So if you are very happy with Leopard, unless you're using a PPC, there is little reason to rush out right away and get it. Yet, at $35cdn there is very little reason NOT to get it either.
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