I actually have that tool for the pedals. It's definitely my most specialty tool.
Anyway, I hit a major snag. I went for a couple hours yesterday and had no issue. Mostly empty road but 2 miles of city to get out and back. I didn't have any issue and totally think this would work.
However, upon returning home, I noticed the recently repaired shoe was separating from the sole again. I've gotten the impression that these weren't great shoes. I don't think the local cobbler was in his element in fixing these either.
I opted for a mechanical connection using two provided vent holes and one I drilled. I drizzled a bunch of plastic/leather/vinyl cement into the gap and bolted them together. The bolts are permanent, set with loctite. It's a solid connection to the shoe that isn't going anywhere. Shockingly, non of the bolts are felt through the insole.
It does make it impossible or impractical to use toe clips or slotted cleats, it's pretty much clipless only now.