I've never been a Fleck fan. The reason is that seven years in, we are exactly where we were under Kill/Claeys - a play or two away from winning the division (Mason to a lesser extent had a season or two where 2 or 3 plays go differently, we could have ended the year as Conf. champs). Fleck has been all sizzle, very little steak.
One can argue that we're a better team then we were under Kill/Claeys and Mason (definitively better than Brewster), but marginally so. The recruiting promise never materialized (except in June, which didn't even make it out of the week the Sports Communication director sold in the tired story of how amazing our recruiting looks in June each year) and the game is very different today with the transfer portal, etc. than when Fleck was hired.
If you look at the relative team talent levels, the overall team talent is better, but again, only marginally so. The team talent in the Kill/Claeys era was at 12th in the Big when Fleck took over. It's never been above 10th in the 6 years the metric has been measured under Fleck. So while you can argue the talent is better, so is the entire Big 10's talent, save one or two other teams. So we have more of the same until Fleck proves that fact wrong.