Roast my plan to work remotely from Japan for 2 months next spring

I am a 34M software engineer from London looking to spend some time absorbing day to day life in Japan, food in particular. I've been before, I spent 3 weeks travelling around with my wife hiking and exploring, and of course I want to go back.

Work:

I am able to work remotely for my company anywhere in the world. My working hours have to overlap with London mostly, so in Tokyo I would be working roughly 3pm-11pm. These strike me as pretty good hours, I have all morning free on work days. I will only work 3-4 days a week most weeks, using paid time off to lengthen the weekends.

I am aware of the digital nomad visa and I do qualify for it. but I was thinking of just flying under the radar on a tourist visa. EDIT: I will be applying for a digital nomad visa.

Housing:

I've found airbnbs that are approx 210k yen per month. This is a little on the expensive side compared to local Japanese listings but they are all bright and in good condition, come with a decent kitchen setup and a table for me to work on. I'm happy to pay a slight premium for ease of booking and having airbnb support but I hope 210k isn't total robbery

Language:

I speak basic travel Japanese now. I can order things, ask for help, count, and use good manners. My vocabulary of food items and ingredients is very good. I'm going to keep learning more between now and travelling. I'd like to be able to hold a short small-talk conversation about food or weather or the local baseball team before I travel.

Social:

I want to improve my Japanese as part of the trip but I think I will need to hang out with some English speakers at some point. On meetup dot com it seems like there are plenty of casual soccer games I can play in and tech meetups where I can chat to some nerds. Worst case I can head to a British/Irish pub at the weekend and watch some soccer on TV with whoever is in there.

Where am I going wrong? What haven't I thought about? Thanks for your help

by elgrovetech

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