Steves' tours are a small part of his operation, which is mostly the guide books he puts out. I find that the books are kept current and they often have real gems-Fodor and the others tell you when the Louvre is open, but Steves tell you the secondary entrance that usually isn't crowded.
I'm not sure what to make of comments like finding his product distasteful or his website appalling. Guidebooks distasteful?
I doubt Rick Steves worries much about being considered uncool. An article on him in the Sunday NY Times two or three years ago said he grosses $30 million a year, and I'm guessing there's a 15-20% margin on those books.
Now that's very cool.