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Sounds like you have a good e8400 already. Not sure how much higher you will go with an e8500
My current E8500 does 4ghz at 1.264v easy but (I'm blaming the board...)
Which motherboard, RAM and Heat Sink are you using? I am planning to buy an new Rig and I am pretty much impressed with the perfomance of E6400-E6500. But still skeptical about the combination.
http://www.hardforum.com/showthread.php?t=1327713
my E8500 lapped with some arctic silver 5 and a lapped ultra 120 extreme with 2 80cfm 120mm fans let me take the chip to 4.6ghz.