Not sure of the specifics of your guys' argument but if I may, I'm going to respectfully challenge your general line of thinking, NarrowJ.
I know a guy (well I know his wife) who was a huge Cubs fan and stat geek. He got some of his analysis in front of the Cubs organization and a few years later he had a World Series ring and was riding with Theo in the parade. He started out as a fan with a hobby.
There are also several examples of fans who start with personal blogs and become respected analysts over time.
If someone has enough time and passion, they can become pretty knowledgeable about a subject.
Brad Underwood has forgotten more about basketball than any of us will ever know. This is true. But fans, especially ones as passionate as ours, are certainly capable of analyzing a situation and providing a somewhat educated perspective. Especially, I would say, on the macro things. Sometimes I think a bit of a "can't see the forest for the trees" thing happens with players, coaches, and yes even insiders.