Michael, I have been going through the lighter footwear transition for a few years now. I took it in a couple steps going from heavier footwear to much lighter Hoka mids to La sportive trail runners. I have a tough time finding shoes that feel just right but IMO it is essential to get a pair that feels perfect from the start. I have never owned a pair of shoes that felt better or magically resolved their initial problems with more use… so called “break in”.
I found strengthening of my foot came with simply hiking more miles and in the shoes I wanted to be wearing, which would be the lightest and most comfortable at the end of the day. For me some key factors were decent cushioning and a well fitting shoe around the mid section and heel of my foot to control hammering of my toes on the downs. I hike the same kind of stuff Bob illustrated in his pic above and find a decent bed of eva foam is just as good as a shoe with a stiff hard foot bed for easing the woes of hiking rock and roots all day.
My current shoes are La sportive wildcats and so far I find them pretty darn good. Very comfy with lots of toe room and very well fitting…no toe bumping on the downs. The soles are pretty grippy but not as good as my Hokas were. There are compromises to be made sometimes. In fact I have another pair of La sportivas that were absolutely terrible on slippery rock and I just kept them for front country use or short walks around the house. So even within the same mfg. you can have huge variances. I would strongly recommend buying from a store you can return used items to after you give them a test drive. You will save a ton of $$ and worry.
Also with different gear sometimes comes different techniques. Simply picking good lines and stepping down on as much flatter softer ground as possible can save your feet a lot of punishment over thousands of steps each day. I would go with the trail runners and ease into using them. Once your comfortable with them chances of returning to heavier footwear will be slim.


