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once you start looking at ones with similar designs to the Mac (slim, metal case, etc)
See, I use it quite a bit every day so I'd rather be using something that feels and looks nice and I am willing to pay a (certain amout of) premium for that.
I tried using cpuboss to compare the performance of the processors but pple seem to be quite vague about what the processor actually is.
M_V-
See here http://browser.primatelabs.com/mac-benchmarks
Your 2008 iMac gets 1654 single core and 2976 multi core (32 bit)
The 2016 15" MacBook Pro (2.5) gets 3180 and 11959 on the same tests.The new chips are way faster. The ghz numbers mean nothing when comparing between different chip generations. This link may be useful for explaining i5 vs i7 etc. http://www.trustedreviews.com/opinions/best-intel-processor-core-i3-i5-i7
My main thought would be decide if you need a laptop or not first. You get way more performance for your money if you don't need portability.
JonD
GHz numbers don't mean that much. Try looking on http://www.cpubenchmark.net for the processors and see what scores they get so you can compare them.
You get a lot more for your money with windows, although once you start looking at ones with similar designs to the Mac (slim, metal case, etc) the price difference isn't as great. If you don't care as much about that though then Windows is perfectly stable and usable nowadays