I do feel fortunate. He is old school and expensive. I am also fortunate that the expense is no longer a factor for me, even for less expensive cotton garments. But all your points are very well taken.I read that ⇧ and immediately looked at your location. My kingdom for a great tailor.
What I've found in NYC in the last several years are (1) bad inexpensive tailors, (2) bad expensive tailors, (3) some okay-to-good expensive ones and (4) some good very expensive ones - but no great ones at any price.
I used to have good inexpensive ones and great expensive ones, but they've all retired or passed away.
It's not simply a matter of being "cheap," but having to pay a lot of money for good not great tailoring changes your purchasing equation as some inexpensive garments that would work for you with a little tailoring become not worth it as the tailoring makes the all-in price silly for the quality of the garment. Also, it's frustrating to not have a true pro to work with.
NYC’s famous sophistication notwithstanding, high rents and overhead are probably inimical to a robust tailoring industry.