Great little blog, interesting thoughts.
I'm also a fan of both Hitchhiker's Guide AND The Fountainhead, but I have to disagree with you on an important philosophical point: Money should not be a GOAL. Money is a reward that other people bestow upon you when they value your productivity, but Roark wasn't out to make money. He was out to build buildings.
It should be noted that The Fountainhead was not overtly political in nature, either. The theme was individualism vs. collectivism in man's soul. The primary moral conclusion is that you should think for yourself.
Nobody was violating Roark's rights when they refused to hire him because he refused to design ugly buildings. They were, however, not judging his buildings on their artistic merit, or engineering soundness - they were judging his buildings by the standard of mediocrity that everyone else expected, and nobody dared to rise above.
Roark ended up working as a day laborer in a rock quarry. For him, it was better to struggle financially and take difficult jobs than compromise his artistic integrity. He didn't care about money, except when it provided him the means by which to be creative on his own terms.
There is a very important libertarian theme expressed early in the book, and it thankfully made it to the movie adaptation as well. In a boardroom Roark is confronted with an extremely difficult choice: Sell out to his clients for a great deal of money and fame, or refuse a commission. One of the board members says to Roark that it his his DUTY to serve his clients. He's shocked by this and proclaims: "I don't build buildings in order to have clients, I have clients in order to build buildings."
How is this libertarian? It demonstrates the principle of mutual exchange, value for value. Workers are not slaves to their employers, and neither are employers slaves to their workers.
The philosophy of individualism and it's essential values of entrepreneurship, self reliance and critical thought are very eloquently dramatized in The Fountainhead, and not so much in Hitchhiker's Guide. Hitchhiker's Guide is silly, fun, and has lots of libertarian jokes in it, but I don't consider it a philosophical treatise.
I would be more interested in a comparison of Robert Heinlein's "The Moon is a Harsh Mistress" and "Atlas Shrugged", the two most important libertarian fiction books ever, in my opinion. Maybe you could write a blog about that?