Well for starters, identifying the actual truth about a subject informs the public. And since the Red Wings, like all other businesses, are dependent on the public for revenue they are generally are very amenable to public opinion.
Those types of questions also help inform management too. One of the biggest mistakes any decision maker can make is thinking that their way is the best way, or their thought process cannot be criticized. The press acts as a sounding board for decision makers all the time. Ken Holland is not different.
Finally, asking relevant questions and ensuring that the answers provided are accurate and reliable is also the whole point of having journalism in the first place. If you'd rather they didn't ask questions, then why do you bother reading news? Just have the Red Wings twitter and facebook posts sent to your smart phone and move on if you don't care if the news is accurate or not. However I suspect, since you do go out of your way to consume news (by your own admission), that you'd likely prefer that the news you get is being collected and distributed in accordance with best possible industry standards and not just phoned in.
But you're acting as if, if the right questions were asked, Holland would be all forth-coming with "the truth".
He has his famous sayings.. "I like our team" etc. for a reason. They don't have to answer to us whether we like that or not.
Success has granted them some leniency in that department. If that continues downward I don't expect them to turn to their fan-base for direction.
Again, I read the Wings media reports to get updates on players (reports, stats, facts) and read opinion pieces to better reflect on my own. Not to read Holland Q&As.