1) He's not a hypocrite in any way. He's honest and you can tell that he has truly thought about his opinions.
2) In my country, I get bombarded with a ralentless stream of leftist ideology. The worst kind of leftism: the lazy 'slogan' leftism, from people too stupid to realize the full implications of their discourse. In comparison to them, Stallman is a moderate, thoughtful, sweet person.
3) I see his leftism as orthogonal to his software freedom ideology. I use and support free software, and I'm more pro-capitalism than Milton Friedman.