Today I figured out skyscanner. I saw it all the time before, but never realized how powerful it was.
This is the formula of power:
http://www.skyscanner.com/flights-from/(airport code goes here!)
You can use sky scanner to find the cheapest flights from a specific airport to anywhere. This is a huge boon if you are 100% flexible in your travel & you have budget requirements.
Another thing that I also figured out is that finding cheap multi-city flights is the ideal thing to do because these flights can later be converted into extended stayovers at the purchase site you end up at (ebooker, vaya, orbitz, whatever). Basically just choose the multi-city option and re-input the flight details, but stick a few days in between. Probably have to play around with different days, but you can usually get at least 2 day stay overs for free or a few bucks more.