Yeah. It takes ~$10k to dirtbag around the world for a year if you mostly stick to the developing world. The equation then is how long need a fella work an on-site contract for a Silicon Valley or SoCal rate, while borrowing a couch or renting the cheapest room available nearby, in order to save that much?

Keep in mind, that your taxable income for the year will likely be less than $20k, so most of your paycheck while you're living cheaply will go straight towards travel expenses for the next lap.

Personally, I liked 3 month contracts. I usually ended up saving a lot more than I could possibly spend on the road.