It might not be the best place for the Olympics (but you know that NYC had a bid in 4 years ago and most of the problems that will be for Tokyo would have been the same). But I loved visiting Tokyo and I would like to address some of the OP’s issues:
- It is crowded in a way that would make a Chicagoan nervous.
Similar to NY, in fact.
- Everybody smokes cigarettes, with few restrictions.
Sadly true.
- English is rare, and most signs are in Japanese only.
There are lots of signs in English. Subway stops are labeled in Kanji, Kana, and Roman script.
- The train system is fantastic, but impossible to learn for a foreigner.
No worse than NYC, good signage and good maps.
- It is a male dominated culture, women are still second class.
It may be, but it doesn’t impinge on tourists.
- The weather is unbearably hot and humid, with a cold winter.
The winters are mild, especially compared to Chicago. Nights might just get below freezing and days generally well above. I haven’t been there is the summer, but I imagine it is a lot like New Orleans. In fact, I think it is generally like New Orleans.
- Most men work well over 40 hours a week.
At least they need only one job to support a family.
- A beer in a bar costs at least US $ 20. Food is also incredibly expensive. If you only speak English, it is impossible to find inexpensive noodle shops.
That was what surprised me. I found the food surprisingly reasonable. Hotels were impossible. One restaurant I frequented had fixed meals (you chose meat or fish, but otherwise no choice) charged 1000 Yen (about $10) for dinner and another couple hundred for a bottle of beer. In the airport, I got a nice steak dinner for about 2000 Y. Noodle places were easy to find. The staff likely wouldn’t speak any English, but most places had pictorial (or even bilingual menus) so it wasn’t that important.