All good points in terms of coaching, but by your logic Collins at NW should be near the top of the Big Ten. He was an assistant at Duke, so he should be dominating because he had experience from the best.
Some coaches have it and never experience it until they get to the Bigger Leagues. I look at coaches like Turgeon, who was an assistant at several places, his first head job was at Jacksonville st, WSU, Texas A&M and then finally Maryland. He has been all over the place and had success.
Bens only two stops are at UND and UNI. He has found a place to coach and if you can continually build success in the MVC you will be a good coaching candidate to move up. Look at all the good coaches to come from that league. Dana Altman at Oregon, Doug McDermott at CU, Matt Painter at PU, Cuonzo Martin at CAL, Keno Davis Directional school MICH, Tubby Smith Texas Tech, and Barry Hinson (SIU).
So there are several good coaches who have made it out of that league and I think Jacobsen would be right there with them. He can surround himself with good coaches and he has the pipelines into two major recruiting areas in the midwest. Yeah he would take his lumps early on, but I guarantee you he would be successful wherever he is at. It might take time at some spots. You look at the Big Ten teams who are struggling, are any of them in a bad place (Minny & Rutgers). Those two jobs would be tough to build, but could be done given the right amount of time. Illinois job seems to be a good one, but still going to need some time.
I think Jake could take one of those programs and given 3-4 years could turn it around.