This active income can help me fund my retirement as well as help me get reimbursement for home office and health care premium while lower my tax liability.

It took 2 months and 1 week, including unfurnished and furnish (so from guest out to guest in was 2 months and 1 week).  

If you are hoping that this property will stand on its own with you living in it and not having to put your active income into it, then it might not be the best option for you right now. 

Seems to be decent on Airbnb with the guest house/ADU units with all the hospitals nearby.

For S's and G's, below is the most expensive SFH on the market in Tokyo right now, followed by one of the least expense:https://www.homes.co.jp/kodate...https://www.homes.co.jp/kodate...The condo market is probably more active than the SFH market, but I don't have much insight there.  

Short term rentals are legal when the host is living in the same apartment as the guests and there are no more than 2 guests staying with the host."

I would also pay by activity not by the hour.  

Hey all,My name is Tony, I'm 35, just started actively pursuing financial independence and have been really hammering away at learning everything I can.

He’s got a solid reputation and is an active member of the local REIA.

You can look up comparable rents on active zillow for rent listings or on Rentometer.3.