A few deciding factors. If you have a great dual-clocking board, like the Biostar T-Power I45, and are using air..then no. The E8600 is worth it with LN2/DICE/TEC, due to the 10x multi. I know of a few people who've hit 5GHz with E8400s on air....though not stable, of course. The other thing to mention...if you have a board that doesn't like 500+FSBs, again, the 10x multi will get you a lot farther than an E8400. IMO, the E8500 isn't a decent option...either get the E8600 or E8400.
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