TBF I've done single day small tour groups with local guides, and when the guide is good, the experience has been amazing.
Doing it first day in Mexico City was actually super useful to get myself orientated and to get a good overview of the mass transit system there, and also to get a list of other things I should do.
Plenty of people from all around the world go on "tour bus" types of tours though, I'd say that before Google Maps and online resources, such tours were likely more popular. You still see huge tour groups at any popular destination, oftentimes grouped together by nationality.
So I'm not averse to doing things that way. And I'm not doing some &^#$Q@ bus tour. But if you want to see the countryside and stay in an onsen* and all that, it's not quite as simple as "someone has good English". I've encountered places in all those where nobody around spoke good English, and we made do in another language and Google Translate. Assuming that, of course, you have good cell service - which was a problem when I tried to drive into a restricted area of old town Krakow. The police officer was polite and helpful, but we didn't share a language and cell service was slooooooow. And Google Maps was absolutely dead wrong about routing and cost me an hour of driving around in a circle (it was rush hour, so traffic, and it though certain roads were connected when they were not - this was only five or six years ago, so not ancient history). My hotel was in that area, so they let me through.
My concerns may be overblown, but they're not arising out of some complete ignorance of how the world works.
It is bizarre, especially the stuff about the addresses. Has the OP never heard of Google Maps? You just point it where you want to go and it tells you how to get there. No one in Japan cares about addresses; the only thing those are really important for is addressing your mail.
But I don't think his mentality is unusual for Americans who contemplate foreign travel. They really do think they need to hire a tour guide for a week to get around in a foreign country.