Is there a program that tells me the best overclock settings for my system? "Settings that have been tried and found sucessful"

nope, you cant really design a program like that, a setting might be stable but may cause artifacts to occur when rendering an image and the program couldnt know the difference.

depends on the board. most will come with the software. gigabyte has a overclock program called easy tune. It lets you up the fsb while in windows. or you can hit one button and it will give you the best setting for the cpu.

Every CPU is different. CPUs are created to be a certain speed, are tested at that speed and then, if they fail, they are dropped down to slower speeds and they are retested. This may mean a CPU designed to run at 2Ghz may be sold as a 1.7Ghz That 1.7Ghz CPU may be fairly stable when overclocked to 2Ghz (the level it was designed for) but not quite stable enough to meet the manufacturer's requirements. Anyway, that is why you can't write a program or publish data telling you exactly what settings your CPU can be overclocked to. The 2Ghz CPU may have been designed to work at 2Ghz and be maxed out right there, or it may be a 2.5 that failed a couple of tests and was dropped back to that level making it more overclockable (if possibly a little less stable in some aspect or another).