Rob Greenfield went on a cross-country bike trip across America, and pretty much lived from dumpster diving. He dumpster dove 70% of his food!
Would you consider making a trip like this? If so, would you go full on freegan, or would you budget some money in for buying food?
You might want to check out this previous entry, which looks at the various barriers faced by people who would want to go skipping but are unable to. It really helps put stuff into perspective, and allows those of us who can and do dumpster dive to recognize it as the awesome privilege it is.