I hear you on the laces. Have a pair of Rancourt ranger mocs and love them, but the leather laces were stiff and awkward at first. But they start to soften up nicely, and I'm sure that rigidness just means they'll last longer!
I'd take it a step further even. It's very much about people's perceptions of the wealthy differ from region to region. I grew in Southern California - the signifiers of true wealth at that time and place were weather you could walk around in a Polo shirt, not a Brioni suit and a walnut dial Rolex. I also don't run around in moneyed crowds, but I have to think that if you're in an industry where your opinion of someone you're about to do business with fluctuates depending...
Just placed orders for two makeups (one for spring/summer, one for fall/winter) with Dustin at PDG. I'll definitely post pics when they arrive. Dustin was fantastic to work with by the way. I've had a great response on emails from Katie at Rancourt in the past about what's available, but given that some people have suggested they're a little bogged down at the minute, thought I'd put PDG to work for me!
Agree 100% on the break in - leather is stiff as he'll even after 8 or so wears. I don't have the heel problem though. More finding that the toe box leather is not relaxing at all and definitely agree the double sole hurts the flex if the shoe. But I got it for foul winter weather and it's held up well in nasty conditions so far. Hoping I can eventually tame these beasts!
I agree. If gemming was indeed an such an issue I'm sure there'd be a mass of SFers with virtual pitchforks in hand demanding why their English and Spanish shoes were falling apart. And I have never wear tested a shoe under your proposed conditions but I suspect rotating only two shoes over 20 years would lead to some beat up looking kicks gemmed or non-gemmed.