This is 100% conjecture on my part... But I think you're probably right on the portal vs high school kids route with Woodson. Some of the things he's said, some of the interviews I've watched, I'm guessing he doesn't like the process of catering to high school kids that haven't proven anything yet. He just started coaching college ball a few years ago, but he's older, and has been around the game for a long, long time. And most of that time has been spent around NBA players and organizations. It isn't too much of a stretch to believe he has a chip on his shoulder having to treat these 17-18 year old kids better than he had to treat grown men professionals.
And then I do think the style of play, both from the B10 overall, and from his own teams play, have hurt him with a number of scoring and/or shooting oriented perimeter players. And then, I think my first theory on his personality and attitude not jiving with how kids need to be recruited nowadays, probably also plays a role when he's trying to talk through his offense and his style, with kids and their parents. I could see him growing very weary and tired of having to justify his beliefs to kids and their families.
We're seeing the end results. Hopefully this team answers some of these things for him, and rather than explaining things over and over, he'll just be able to show them tape. As of now, he doesn't have any tape of having a perimeter player friendly offense.