Like most analysts, be they more statistically oriented or more qualitative/scouting based, there are things I think Hollinger has assessed quite well and things he has not (his whole draft outcome model seems to have some big holes for instance). He's not a scout or GM and probably does not pour over hours of film (he may, not sure about this), but, I assure you the guy does watch games and knows his stuff as well as most of his ilk. I'm assessing this from a couple of conversations I had with him at social events during conferences, so I certainly don't know his specific habits. But, in conversation, he's not some stat geek who does not understand the game, and he does not give off a vibe of being arrogant or all knowing. Pretty decent, engaging guy who seems pretty bright.
Hollinger gets trashed a lot, and in some areas I agree this is deserved. But painting him as a stat focued no nothing sometimes, just has not rung true for me when I've talked him, for what it's worth.