Maybe your experience is different, but what I'm saying is that there is nothing to get proficient at. I mean, assuming the machine is operating properly, there is nothing difficult about walking in stilettos because they are stilettos (on hard pavement at least). In fact, some things are easier than when wearing thick block heels. My issue is the absolute steepness. I hit a wall at about 4 1/2 inches. If I'm really being honest with myself, it's more like 4 1/4 inches. I had to do a quick run to the grocery store yesterday afternoon, and I broke out some round-toed, 4 1/4 inch stilettos that I hadn't worn in a while to run the errand. Once warmed up, I was brilliant. I even got a sincere compliment from a man (how often does that happen?)! But, at that height, I can feel my achilles tendon straining, especially the right leg, with each step.
To be fair, I weigh a mere 60 kg. Perhaps thin heels react differently to more torsional force than what I subject them to, but I don't really notice the difference except when I step in a crack and ruin my heel!
BTW, are towpaths actually used for towing these days? If so, by what means?