I got into a discussion once on that very passage.
It is not about Jesus praising the man for his actions, but praising the man for being a thinker, not what he did, but the fact that most believers do not think ahead.
This sinful man, who ripped off his master by excusing away his masters debts, was not praised for being a thief, but for being a thinker.
The final passage here which you posted, seems to be a call for US to make friends of the unrighteous, so that when they fail, or fall, we can lead them to salvation, not embrace their failure or living, but befriend them while still being someone who is not of their failure.
That would mean we should stay out of CCM, don't ya think?
I would agree with most of your assessment. The only part I would disagree with is that I think our Lord Jesus is telling us that non-Christians are very clever in how they manipulate one another as the unrighteous stewart did. I interpret this passage to say Christians likewise should shrewdly use whatever means available to send the message out. If that is the case I would say using Christian Rock is using worldly tools very wisely and I would say the Lord would want us to use these types of tools.