I find it interesting to see that lack of knowledge about economics (Greece is not in deep shit because of the welfare state) and adoration of a business man like Offenhouse go hand in hand.
About the two ways of life clashing, Picard advocates knowledge instead of power, fulfillment, letting go and enjoying his life instead of being control-hungry, anally-fixated and feeling empty and helpless without his job and money. It is fairly obvious which way of life is better.
About your point concerning "being your own man", well, I don't disagree about the principle. But Offenhouse is not a confident man, he was hysterical, unwilling to listen, accept the new circumstances and adapt to them. The musical dude on the other hand had no problem to be true to himself and adapt to this new life at the same time.
I'm one of the best doctors (engineers, educators, thinkers, etc.) on this planet and it is a joke that I have the same lifestyle as someone who dropped out of school when they were sixteen to sit on a beach, surf and screw.
You can hardly be the best doctor if you are motivated by envy or money. That makes you wanna get as many patients as possible through during one day which implies bad quality care. But hey, it also implies this Ferrari you want so desperately.
We never saw any of the five doctors on the shows enjoying a luxurious lifestyle. They are the equivalent of doctors going to third world countries today, they don't it because of the money but because they love their job and actually wanna help those who most need them.
Same with the engineers. Scotty reads tech manuals during his break, the guy is a total workaholic. He loves his job and not some yacht or whatever.
As we already discussed work incentives previously his thread, Offenhouse is just another example of a person who does not work purely for the sake of consumption. So make up your mind, either Offenbouse is your hero and people work for other reasons than consumption or he is not your hero and we are back to Econ 101, labour supply as a consumption-leisure trade-off and the yacht-craving doctors. So in order to provide an internally consistent argument you have to make up your mind.