Since last May I've been spending increasing amounts of time in Perú doing just that. Recently I've finally made the move more "permanent" as I've rented a house here in Lima and plan on staying a least a year.

The easiest way to go about it is to maintain your permanent residence in your home country and enter new countries as a tourist/visitor.

This officially means that you can't "work" in the country you are visiting. However, as long as your clients are not local and you get paid to your bank account in your home country, you should be ok.

I would highly recommend you review your tax situation for your country, and especially the country you will be visiting if you want to stay longer than their tourist/visitor visa allows.

I'm going through all this myself and have started blogging about it at http://expatentrepreneur.tv ... A lot of other people blog about the expat digital lifestyle. One I enjoy reading is http://exilelifestyle.com and he has links to quite a few others.

I highly recommend South America to you... it has a fast-growing tech/startup community (Chile, Brasil, Argentina, Peru) and there are tons of expats as well.

If you make it to Peru feel free to look me up!