I don't trust OC utilities, if you want to OCing then do it by yourself in BIOS setting, play with multiplier and FSB...
For your problem, try reset the CMOS battery, unplug it for 10-15 minutes, after that plug it again and boot normally...
OCing is basically the same, you can use OCing thread (sticky) on this forums (overclocking section) to guide you OCing your i5.
And 50'C idle and 65'C full load is HIGH, you even not OCing your CPU yet...
If you are at 50C at idle, you are running too hot.
Before OCing, did you stress test your rig to find its limits? To resolve cooling issues?
If not, run Prime95 using CPUID's Hardware Monitor to watch temps. Do not go over 75C core temps for too long. If you can't run an hour, you installed the cooler wrong, or your case has bad airflow. You need to resolve that before tyring to OC.
I have antec 900 i got it due to its good airflow, i mean the damn thing actually has cooled down my room by about 4-5 degrees F, i have Great cable management for a non moded one, with a modular power supply.
What could i of messed up with the stock cooler? Should i just rotate it 90 degrees
That's better than last reported, and you're good to resume trying for a mild OC. The 66C makes me think you will need to install a custom cooler in order to achieve much in the way of an OC, and keep temps under 75C under stress.
So go slowly. The Gigabyte utility has a three step OC, and for the most part only the smallest OC option works "well". Voltages are often a bit higher than they need to be. I'm not familiar with the Asus utility, but a 10% OC is about the most I'd attempt given your current temps.