I can't argue with your opinion that Courtney's are old technology. They truly are 1980s technology, no synthetics, no membranes, etc. We can agree to disagree on whether that is a feature or a defect until we empty a bottle of bourbon together.
I would debate the "overpriced" comment. A handmade boot in select leather (exotic gameskins no less) for $350-$380 is in my opinion, an absolute bargain. Russell Moccasin can make you a different design with the same quality leathers, soles, and hardware right here in Wisconsin, USA. You'll pay $800-$1200 for those boots of course, but that is what the cost of goods plus reasonable profit demands.
Keep in mind, a Kennetrex or Merrill probably costs about $8 to make and they run off an assembly line. Same for a Nike or a Converse. The majority of their costs are not labor or materials, its sponsorships, marketing, logistics, dealer channel, consumer packaging, and advertising that eats up the other $150-$250 in cost of goods sold.
We might not like how much hand crafted items cost (materials and labor) but this has always been the issue, it's why our grandparents got one pair of shoes per year as school kids. Even then, the costs adjusted for inflation were roughly what the Courteney Boots cost today
Schuhe bei Hallux Valgus. The difference is that today we are able to buy third-world mass manufactured footwear for 1/10th the price our grandparents paid (adjusted for CPI) for US made shoes in 1930.