Overclocking SB is easier than any processor in history outside of XP2500+ (or at least off the top of my mind). I think you are way over-complicating things. All you need to do is adjust load line calibration to enabled, set VCore to 1.35-1.38V, set a lower RAM:CPU ratio and crank Multiplier to 44-47x and you are done. You may need to increase CPU PLL voltage for multipliers 48-50x.
The other part is using VCore offsets at load, but you should do that AFTER you figure out what voltage you need to be stable at load. That's the "tuning" stage.
It absolutely is NOT difficult to overclock SB CPUs. Overclocking has never been
easier since you no longer have to worry about locking PCIe, playing with northbridge or southbridge voltages, playing with RAM ratios (since memory bandwidth is no longer important), tuning QPI/FSB frequency (those are not important either).
Honestly, if you are that worried, just get a MSI P67/Z68 board. They have excellent 5 second overclocking button (and also Gigabyte and Asus boards have automatic overclocking). Automatic overclocking works pretty well but tends to be on the conservative side, both in regard to upper frequency ranges and applying too much voltage.
Just look at this excerpt from HardOCP review:
Overclocking
"Ill keep this relatively brief. Overclocking the P8P67 is a lot like overclocking any other Sandy Bridge setup and certainly just like overclocking the rest of the P8P67 family. Ive done that a lot now so I pretty much just go right for what works. Even with that said, the P8P67 was very nice to work with. I started off by setting the DIGI+VRM control for "Ultra High" and the CPU current control to 130%. With this alone I was able to hit a multiplier of 47x without doing anything other than raising the multiplier. The voltages came up automatically. I hit the wall there.
This was the limit I had seen on a few other boards. After enabling CPU PLL overvoltage I was able to go higher. I eventually hit a speed of 4.916.2MHz with a 49x multiplier. I didnt even have to adjust the CPU voltage manually. It automatically came up to 1.416v which is where I ultimately needed to be anyway. I tried to hit 50x on this CPU to no avail. No matter what settings I tried, manual and otherwise it wouldnt do it. I had never seen this chip do that, so I might have simply been at its limits." ~ Full review