Not sure where this idea that Whitman is a green, inexperienced kid comes from. If I'm not mistaken, he has the most experience as an actual athletic director of anyone on that list of 7.
People are looking at Whitman's experience at Div III schools and equating it to being the AD at someplace like Millikin or Illinois Weslyan.
Wisconsin Lacrosse is a school of 10,000 students that participates in 17 different intercollegiate sports. They don't offer scholarships, but otherwise in terms of number of staff, students, facilities, and so on, it's very similar to non-BCS division I public schools, like a Missouri Valley or MAC school.
Wash U is even bigger, 14,000 students, with more sports and a much bigger budget. As one of the "Hidden Ivies" they get a ton of alumni support. In Whitman's first year there, they broke ground on a $55 million multi-purpose athletics facility.
Yes, going from a year at Wash U to U of I would be a big leap. But it wouldn't be THAT big of a leap. The more standard career path would be for Whitman to transition from Wash U. to a lower tier Div. I job (like a Moutain West or AAC job) or as the top assistant in a big-big time job (Texas, Stanford, Michigan, etc.) before taking on a Big 10 school, but this wouldn't be as extreme a step up as people want to make it out to be.
The only thing that would really bother me about a Whitman hire is that it could have been done two months ago, and then we wouldn't have had to deal with the Cubit nonsense.