My wife and I just completed the trail. We didn't start in Crandon. Instead, we started just west of Pound, WI. This added around 100 miles of trail. I'll include the GPX file for anyone interested (I use Gaia for my mapping software). We were able to complete everything except the section of trail in northern Wisconsin by the UP border. We made it past the first creek crossing, but the second one was really bad. The creek diverted onto the trail and was about 50-75 yards of knee and thigh-deep water. We did not attempt it because we were alone. However, we did go around and backtracked to the other end. We cleared some downed trees, so if anyone makes it across it should be smooth sailing.
Edit - I had the wrong GPX file for the +100. It's been updated to the correct one.
GPX viewer