Getting from Harajuku to Aoyama is a 10-15 minute walk down one of the nicest streets (called Omotesando) in Tokyo. Or one stop on the Chiyoda line, from Meiji-jingumae station in Harajuku to Omotesando station, if you're in a hurry.
I've never had a problem on the ordering side. I've never had to try a return, but if there was ever an issue, I would not hesitate to initiate a credit card chargeback if he did not reply to an e-mail requesting to return an item.
It looks completely appropriate. The fact that you are wearing a tie puts you in the upper tier of physicians these days. Blue shirts work best with white coats and that's what I wear in clinic 95% of the time (occasionally lavender or pink).
I suspect that he spent too much money on 25 colors of canvas bags and other poorly selling items like $600 synthetic raincoats and cashmere baseball jackets, and is now focusing on more popular things like the trousers. Not sure how that explains his non-responsiveness. I hope things are OK in his personal life.
I think the Made-in-USA pants are made by Hertling. I did a google search for some Italian text I found on an overcoat and turned up an article about a factory in Italy run by Bangladeshis who make clothing for a variety of Italian brands.