My first trips to Japan were in 2007. I work with a drum & bugle corps based in Tokyo. I have visited 3 times a year from 2007 through 2019 (and now starting again next month). Since my visits are business-related, they are almost a carbon copy every trip...5-6 days in length LAX>NRT on UA 32/33 (except next month, as they JUST canceled UA 32 3 weeks out...not happy), almost always take N'EX to Shinjuku (bus a few times due to typhoons...those are fun), always stay at Hilton Tokyo in Shinjuku.
First thing that hit me as "whoa" was, and still is, stepping out of Shinjuku station onto the main drag facing the LUMINE buildings in the early evening! All the lights, the massive crowd, and me sticking out at 6'3" and white. Something about that energy is amazing. And taking the cab to the Hilton a few blocks amongst the madness.
We train from Seibu-Shinjuku (another killer intersection with massive video) to the facilities out at Higashi-Yamatoshi, kind of a common outer-city location. Like I said, every trip is very similar, but I haven't gotten sick of it at all. I have hardly ever (maybe never) had any sort of negative interaction with anyone in Japan. We have our eating zones, quick train rides to Harajuku/Shibuya are fun. Killer ramen at Jangara. Like I said, mostly carbon copy but fun!