Okay, I suppose I could answer the question, here is a way you could do this...
Let's use Asia as an example. It's super cheap to live in a place like the Philippines. I'm in a two bedroom house in a great city for only $120 per month. I can get by on food here for about the same as rent or less. The visa costs around $60 per month average but you can stay here for 16 months before you have to do a visa run.
Want to travel more? That's another area where the Philippines shines. You can fly anywhere in the Philippines on domestic flights for like less than $30 per ticket and often much cheaper. You can get flights to places like Hong Kong, Singapore and Bangkok for as low as $60 each way.
With cheap expenses like that, your travel companions could live with you in a foreign country while you ditch them for other trips, while keeping your place in the Philippines as a base between travels.
Working is tricky. Bad economy means most things have bad pay. With expenses so low, it wouldn't take much to figure out how to get by with odd jobs done remotely through sites like Odesk or Elance. I hear foreigners can get call center gigs (likely some sort of language training / management) here. Also, there are lots of Koreans who will pay to learn English (the reason many of them are here) but they likely won't pay much. In any case, you really don't need much to get by.