@racinbob We rode through that area a couple years ago. Before we decided to have a campground base, we rode from my buddy's place in Shullsburg up to Lacrosse, and then back the next day. We ate lunch at the brewery. We fell in love with the Driftless Region on that ride.
@mr-ontop local recommendation, Thai house. Portland/weekender/touristy recommendation, any of the breweries on the waterfront.
As for lodging, I've only stayed at Columbia cliff villas, and it was very nice. This time of year, camping is the way to go, and you can find actual campgrounds or dispersed spots all over in the forest.
having driven to las vegas and back multiple times, salt lake city, los angeles, and driven home from washington, i can confirm that there's a definite line once you get far enough west where it becomes 'interesting'. but if you can deal with it and eat miles, it's worth it IMO.
That said, I think your timeline is ambitious. I'd take more than 2 days to drive to California, and I say this as someone who has done one-shot nonstops from Spokane to St. Paul, Salt Lake City to Minneapolis, Flagstaff to Minneapolis, Nashville to St. Paul, Vegas to Wall Drug, and more.