I think a good place to start this discussion is by asking how much money you have on hand right now? $500? $5,000?
Also, consider the possibility of spending 500$ on a plane ticket and 500$ on a cheap place somewhere sunny (with internet). This should buy you about a month or 8 weeks, depending where you go.
And "sunny" is a very broad definition, I've heard Arizona is cheap this time of year :)
Also, can't he find very cheap travel and accommodation using the tools the HN community provides? (flight planners and AirBnB?)