Advice for traveling long-term on the cheap

Last week, my Yahoo! News column was about how it's actually cheaper to travel for long periods than short periods. Recently, a reader named Kim recently wrote with a tie-in question about traveling over the long term:

My boyfriend and I are planning an around the world trip for 2 years. We want to do it as cheap as possible. Where do you suggest we begin? We will make our way around WWOOFing, camping, staying with family/friends, meeting new ones to stay with, at monasteries and at hostels on occasion. We'd like our primary means of transportation to be trains, buses or bikes rather than planes. How much money would you suggest we should have each for a 2-year trip? Do you know of any message boards where people share info, tips and experiences on world travel? I have been looking for some time and haven't come across any.

This is what I told her:

As I say in Vagabonding, WWOOFing and camping and staying with friends is a good way to go. Also look into hospitality exchanges, like Servas, Couchsurfing, or Hospitality Club, which allow you to stay for free with engaged local hosts around the world.

As for your specific questions, here goes:

Where do you suggest we begin?

It doesn't really matter. Some people start long-term trips with a USA road trip, and these are always a fun way to begin (and end) a long journey, and a fun way to say goodbye to friends Stateside. People also tend to go to Europe first, and Europe is recommended as a starter because it's close enough culturally and logistically to the USA that there's less of a "shock" when you start your travels. Then you can go to more challenging travel locales from there.

Personally, I might recommend starting with a crash course in Southeast Asia. Thailand is always a good place to start, and SE Asia has a lot of diversity, is quite accessible and travel-friendly, and will give you a sense for how cheaply you can get around (better in my opinion to start in a cheap place and be shocked by Europe prices than to blow all your money in Europe and not have enough for cheaper places).

How much money?

This very much depends on where you go, and how disciplined you can be with your funds. $1000 a month is my usual estimation, if you stick to cheaper parts of the world. In some places, like India, you can travel on much less than $1000 a month. In other places, $1000 a month will be tough to pull off. But it's a good starting estimate, and once you start traveling you'll get a sense for how realistic (or unrealistic) it is, given your travel habits.

Do you know of any message boards?

Try the boards at Bootsnall.com or LonelyPlanet.com's Thorn Tree. There are others, but those will get you started. Even reading the existing posts, without even posting your own, will tell you a lot.