Here are a couple posts/blogs that i was talking about. Not sure if you'll get time to read them but i find them interesting.
joel on software - this guy writes really well and, from what i've read so far, he gives me hope that my dream of doing this kind of thing can work.
Example:
Coding Horror - Jeff Atwood: another software guy that writes pretty prolifically. He and Joel (the guy above) have a website that they recently released called http://stackoverflow.com/
Example:
Plenty of fish (i mentioned this last night): http://www.codinghorror.com/blog/archives/001195.html
he writes a lot:http://www.codinghorror.com/blog/archives.html
Another company doing the kinds of things that make me happy: http://www.37signals.com/svn/