I think the mistake skip made was making himself moderator. Skip became popular for the same reason colin cowherd got popular their hot takes their soliloquies. When he made himself moderator he highlights the other guest which then removes skip as the feature when it's his show.
The other mistake was involving lil Wayne more. It's a clear pander to a black audience being afraid that the departure of Shannon Sharp would lose that demographic. Lil Wayne, is just not good. He sucks.
On top of that the topics were pretty redundant. Paul Pierce is a good talent but he just not that talent that continues to go viral like Shannon did. Those viral moments drew alot of views for undisputed and it got to the point Stephen a and first take was showing they were under pressure and bringing up topics and guest to compete. They ain't been under pressure any since Shannon joined them.
He never updated his gimmick. Even the Undertaker had to adjust his shyt. You cant keep doing the exact same schtick, especially when its based in shocking people. Beyond that, everybody is doing it now so you don't even stand out. Topics always been redundant, its just that he isnt moving folks like he used to in discussing them. He is
and the game has passed him by. All the desperate, out of touch, moves you listed are a result of that.