I bought these boots unconsciously just a month before setting on a hiking trip to a 3000+ mts (23+ kms) mountain... (it is highly recommended to wear broken boots and shoes since new ones can be tough to walk on) I stepped on then everyday trying to break them and setting my feet to them before going, but I was constantly told by experienced hikers that I might still have problems with them.
I went anyway with them and I did not feel them as rough as new shoes were supposed to feel like. The insole was enough to provide for a little cushioning. At 14kms into the walk I did feel my big toes complaining... but I seriously can't tell if it was because of the boots or the distance climbed (since it was my first time hiking in steep and uneven ground with rocks and mud...) note: a little medical tape around my fingers eased the pain and probably prevented blisters on my feet.
Eventually I got to the camp and them the peak at the next day with no more discomfort from the boots. The next day I walked downhill back to the base, only that we took a different route that took us through "muddy hell" as our feet and part of our legs sunk into mud at some points... truly glad that these boots had ankle support since they never slid off... unlike the shoes/boots of some of my companions. The next day we passed that muddy route again to reach the base and head home. Only souvenir from the trip was a purple nail of one of my big toes.
I wasn't going to sink then in a stream and have my feet wet for the rest of my trip so I didn't thoroughly test that feature, but they do appear to be waterproof since I did crossed some small streams and it did rain quite a bit during the hike.
Overall In happy that I got them. As I mentioned above they probably meant all the difference on my hike... (well them and the medical tape too :P)