Once again, your BSOD at startup and it being unable to POST is most likely caused by your cpu not receiving enough vcore. Just curious, did you set your BIOS settings to the settings I've listed above? Because with LLC not enabled, vdroop may occur and cause instability even at idle.
And yes I believe you may have a point about your heatsink setup. Generally, with a CM212+ you should see idle temps in the mid 30s. However, since your cpu seems to need a bit more juice than others, your temps will run higher than average (since increase in temps is positively correlated with an increase in voltages). I like that you set your personal temp limit at 70, that is a good number but honestly the SB i5 2500k's can go up to the mid-70s (I personally set my limit at 70 too, intel's stated max is around 80).
To be honest, whenever you oc your cpu, you are trading away longevity for performance. So there isn't really an optimal cpu life whenever ocing is involved. However, people have pushed their oc's to the limit, topping out at around 4.8-5ghz @ close to 1.50V. Of course this setup will shorten the cpu's lifespan significantly. Thus, perhaps anywhere between 4.3-4.5 would be a good balance for performance and cpu life. Don't worry about going for that extra 100mhz, for your cpu I don't think the tradeoff is worth it and the performance gain is almost unnoticeable.
Just to sum things up:
Optimal gain: since your cpu seems to like more voltage than others, the tradeoff of higher clock speeds for significantly higher temps and voltages is not really worth it,
4.3-4.5ghz
Optimal temps: Intel's stated max is around 83, but personally I like to keep mine around
70. Again, you can bring it up to the mid-70s no problem, but this should be a warning sign that you are approaching the 80s. Also, keep in mind that running IBT and p95 will cause you to reach these temps, but while gaming you probably won't even break 65.
Optimal voltage: Intel's stated max is 1.52V, but after reading several forums and articles, I would keep the vcore below
1.40 under load. Once again, this number varies greatly from person to person...but it never hurts to give yourself that margin of error.
Don't give up on your oc man! I know you can pull it off, even at 4.2-4.4 you'll notice quite a difference from 3.3
EDIT: Finally found the link detailing the adverse effects of setting a vcore above 1.40V to oc your cpu (posted from Tom's no less!):
http://www.tomshardware.com/reviews/automatic-overclock-motherboard-cpu,3048.html
"We've learned through trial, error, and dead processors that voltage levels beyond 1.45 V at above-ambient temperatures can kill an Intel CPU etched at 32 nm (Sandy Bridge-based parts included) very quickly. Those same processors die a fairly slow death at voltage levels between 1.40 V and 1.45 V (somewhere between weeks and months on our test benches). And we're expecting more than a year of reliable service from the parts we've dutifully kept below 1.40 V. Not all motherboards are perfect however. Voltage instability on a particularly cheap motherboard fried one of our processors when it was set to only1.38 V. Subsequently, you've seen us use 1.35 V for the overclocking tests in older motherboard round-ups, embracing 1.38 V to 1.40 V in more recent pieces covering higher-end platforms. "