Sorry to hear of the trail condition, last time I rode it was in October of last year and the trail was in excellent condition, very well groomed. I agree with many of your observations. Cooper's Landing is not my kind of campground, too congested but my friend enjoys the Thai food. We always like staying just to the west at Katfish Katy's, by chance did you notice if it is still open. Last fall it was up for sale but it's a really quiet and scenic spot along the Missouri River. I like the Katy, it's laid back but it's important that one knows what they're getting and yes, stock up on supplies when you can because many of the eateries and small stores have closed over the past 15 years that we've riding it. Now you need to consider the 550 mile Grand Illinois Trail which would not be a long drive for you to start, far more variety of scenery such as tooling along Lake Michigan right thru Chicago and it's a mix of canal trail, paved bike way and small county roads. But as you said, the company can make or break any tour.
Thanks for sharing.