The Professional Hobo

That's the moniker of a young former financial planner from Toronto named Nora Dunn, whose site www.theprofessionalhobo.com contains a lot of useful information on long-term travel and affording it. She does it through a combination of travel writing, volunteering in exchange for accommodation and picking up work as she goes.
She's been on the road for more than four years, but often spends months or more in one place. Her site contains links to articles she has written for various publications, and blog entries by her and guest bloggers. She may also soon be appearing in a television travel show.
Before leaving Canada she got rid of most of her possessions, and writes about what that was like. So far she seems to be enjoying her lifestyle, even though it included breaking up with her travel mate on the road.
I find it interesting that many people seem to be making a long-term lifestyle of more or less perpetual travel. I admit I'm a little envious, and I would like to read how some of them manage all the financial necessities of life--taxes, insurance, communications etc. Do they have someone at home who has power of attorney to handle their affairs? Obviously the internet makes it easier to handle bills and investments online, but can everything be done online?
This is an interesting site with some good suggestions about travel savings, even if you aren't a long-term traveller.