Heya, Welcome to the forum!
Firstly, I'd suggest turning off all those power saving features you've got enabled. Particularly on the last two screen shots, These features change the clock/voltage of the processor to help save power consumption. However they hinder our ability to overclock and also achieve a reliable result.
I'd also turn of CPU Spread Spectrum.
Manually set your HT and NB Speed, as well as your RAM - This stops the motherboard automatically making any adjustments on your behalf when you make changes to the Multiplier and or FSB.
Next, I'd suggest you set stock voltages etc also enabled load line calibration and set that so that it provides the closest voltage set in the bios (Usually High to Very High achieves this) and then start to raise your multiplier. I'd raise the multiplier a few notches and then try and boot into Windows.
Successful? run Prime95 for 10 to 15 mins on Small FFTs. Stable? restart and repeat the step above.
Prime95 fail or boot crash? Simply up the vCore a few notches until it boots and prime95 for 15 or so mins.
I'd say aim for 4.5Ghz like in your post, and then prime95 it for atleast a few hours and also monitor the temps to make sure that they're within limitations.
How far the overclock will go is usually determined by the heat and the voltage limitations. The more voltage you add, the more heat you generate and thus the more better cooling you'll require. Also adding voltage also reduces the life of the processor, once you start topping higher clock speeds other tweaks maybe nessasary, like north bridge voltages and phasing.
I hope this helps, and I know it's not really in depth, but it should get you on your way!