I used AirBnB in Tokyo and Kyoto in March 2017. It was really hard to find the apartment in Tokyo, luckily we had internet and cell phone access so we were able to call/text the host multiple times to figure it out. The taxi driver dropped us off in the general area, but he wasn't able to tell us exactly which side street of Harajuku to walk down. I would do it again, but I would study the address beforehand and try to figure out what the building looks like on google maps. It was really fun trying to figure out how to use the appliances!

I also had problems making restaurant reservations. Most people do not speak English and I do not speak Japanese, so it was impossible to call and get any information or make a reservation. On previous trips I stayed in a hotel and took the concierge for granted. I think you could get around this problem by using your credit card concierge (like Amex platinum), but it usually takes a couple of days for them to organize things.