When it comes to WI 26, I think WisDOT reacted to the negative backlash they got from some of their on-the-cheap bypasses by going whole-hog on that corridor. Immediately prior to that expansion, in the mid-00's, WisDOT had a number of new bypasses with high crash rates at some of the at-grade intersections. (Fond du Lac, Whitewater) I think that attention pushed them to go straight to the full-freeway build outs for the WI 26 bypasses in the ensuing decade.
Seems like I-94 could very well get some attention from the 5 billion highway dollars Wisconsin will get out of this 2021 infrastructure bill.
I figure WisDOT uses most of it to do the idle Stadium Interchange project, expand I-41 between Appleton and De Pere, and maybe expand 90/94 from Portage to the Dells. That probably eats up a bit over 4 billion; then spread the rest around the state to catch up on maintenance.