Unfortunately, Japan does not offer the same tax deferral benefits for 1031 exchanges as the U.S. does.

He’s affiliated with Dave Ramsey solutions but I think that is a benefit in my case.

Often it comes down to risk/benefit analysis on whether to make a legal claim or not.

I benefit from step up inheritance laws, so almost no capital gains tax if I sell, I do like the idea of liquidating and putting it into a larger property or multifamily, I do worry about the amount of time hands on, which I need to be s minimal as possible.Thanks!

Can you explain what the benefit is to a property owner to have a literal stranger sublet their house to a whole bunch of other strangers and pocket the difference in rent?

Minimal cash upfront, negotiate a monthly rent, lock in a price today that will benefit from any appreciate that might occur during the term of the lease.

A side benefit is that the applicant pays Zillow not you for the application fee and their application can be reused for 30 days to submit to other landlords.

They do the hard work while investors like myself get the benefit of having a long term rental.

I do have a lot of knowledge and skills and small network that would hopefully benefit other investors and in turn would help grow a portfolio. 

No option is really better or worse than the other, they both have benefits and draw backs.