Okay, sounds like it's worse than it looks from the pics then. But the cobbler will fix it fine.
Even if you tops the shoes you should resole them, although you can do it less often. But it's not just the outsole that gets worn, the cork or other filling gets bad after a couple of years, shanks could come lose or break or if made of leather or wood be in a bad condition, etc. So to secure as long life for the shoes as possible you should resole occasionally even if you topy your shoes.
Yeah it's hard to capture. Never seen a cut that deep in a sole before.
I just dropped them off. He is adding in the cement before topying, since otherwise he said something sharp could potentially pierce the topy and begin to pry apart the leather or over time the adhesive may fail in that area.
According to DW, even if you topy you will still need to resole. Along with the above mentioned conditions they tend to grind down the sole a little bit to remove the old rubber cement when they add in a new topy. This eventually will wear through the sole even if the other parts remain fine.
I do topy generally anyway because every city I've ever lived in has been really slippery and wet (London, NYC, Boston ect). The traction is really helpful with stairs.
I'm surprised how comfortable the leather on this pair is. LM must use considerably nicer leather than the classic collection.