[ghaff]

The last couple of trips I took to Japan were for events with essentially a developer/marketing oriented organization and I was able to comfortably get off with pretty much business casual. Maybe I wouldn't have felt as comfortable for a customer event.

The last trip I really felt I overpacked for with respect to train/transit was some time in London, followed by a long-distance walk where I really needed everything I had with me, followed by an ocean liner return where I needed jackets and real dress shoes--which, as you suggest, even Rockports aren't really general purpose. You always want more shoes than you can reasonably carry.

Wheeled vs. non-wheeled luggage is definitely a tradeoff. I lean towards non-wheeled in general and just maybe take a few more taxis if the luggage is too heavy to schlep around the city a bit.