Chris Guillebeau writes The Art of Non-Conformity, covering self-employment, bootstrapping, unconventional careers, and travel.
HN commenters recommend him for insight on self-employment, overcoming fear of leaving a steady job, bootstrapping, and travel, and one credits him for the advice to offer multiple packages.
The blog: The Art of Non-Conformity by Chris Guillebeau (http://chrisguillebeau.com/3x5/), writes a lot about bootstrapping and how he started out, he now has a self sustaining blog and affords to travel all over the world and blog about it. It's a great blog, lots of inspiration, and I think it'll definitely meet your criteria.
Are you familiar with Chris Guillebeau's blog(the art of non-conformity)? He has some great insights about being self-employed and the fear of change, especially for those who have a steady jobs/mortgage/kids/etc. I alwas go there for inspiration and reassurance when I need it.
http://chrisguillebeau.com/3x5/
Multiple packages is one of the best decisions I made. Though I have to give credit to Chris Guillebeau (http://chrisguillebeau.com) for that one. He told me how important it is.
Chris Guillebeau writes/wrote about similar issues. (see this post on getting into Saudi Arabia):
http://chrisguillebeau.com/getting-to-saudi-arabia/
Have you seen this guy? http://www.chrisguillebeau.com/
He shares your interest in travel; you might find it interesting.
He assumes you make more than $2 a day. http://chrisguillebeau.com/3x5/you-are-incredibly-rich/