The CF has always screwed up boots. The old Greb boots were garbage and fell apart after minimal use, especially the soles, as previously mentioned in the thread. The replacements from Prospector were even worse as they were already poorly sized and would the fabric and leather would stretch significantly when they got wet and the lining would separate from the outside layer. The original canvas and leather jungle boots were quite good for the simplicity. I still have and use mine that were issued in 1993. They have taken a beating over the years but are still reliable. The all black, nylon upper that replaced the green canvas were terrible as the seams would tear within the first day of wear. We also had a desert boot, same as the Yanks, and although they appeared similar to the jungle boot, were very different. Too much flex in the ankles and lots of injuries, but they were light and breathable.
I like the concept of having the troops source their own boots however the reimbursement is limited. Troops cant really afford to buy themselves good boots considering a good combat boot runs $400 to $600, resulting in lots of cheap boots like Rocky, Salomon, Hi-Tec, and Bellevilles.
I had Danner Acadia and Ft.Lewis during my time in but was constantly hounded by the RSMs and other fun-cops for "non issued kit". I had these boots before I joined the CF as I used them for hunting. My infantry days are long since gone but knowing what I do about boots now, and if I were to do it all over again, the Lowa combat boots based on the Tibets would be my first choice as a general purpose field boot, something from the Zephyr line for garrison, and the Desert Elites for hot weather and unpleasant deployments. I love the brown Combat boot Lowa made for the German forces and bought two pairs for hunting. Altbergs from the UK would be another great choice and I really like their jungle boots but this brand is not readily available in North America. Unfortunately the average soldier is not likely able to drop $500 on a set of boots.