Also reviving this thread, in a very similar situation as @Stephen G. 

If you want to document how you handled unique situations that could be sensible.

Hi Charles, I'm also based in Honolulu with young kids and in a similar situation to you, have also thought about buying an investment property in Japan that we could use part-time and rent out at other times.

If not try a keyless entry situation that allows you add a temp code that will expire after the work is completed.

I applaud Brian for personally reaching out to respond to the situation and make sure things are addressed going forward. 

Year 0: ($2,000 - $1,700) x (1 + 2%)^0 / (1 + 5%)^0 ≈ $300 in today’s buying power.Year 5: ($2,000 - $1,700) x (1 + 2%)^5 / (1 + 5%)^5 ≈ $260 in today’s buying power.Year 10: ($2,000 - $1,700) x (1 + 2%)^10 / (1 + 5%)^10 ≈ $225 in today’s buying power.Year 15: ($2,000 - $1,700) x (1 + 2%)^15 / (1 + 5%)^15 ≈ $194 in today’s buying power.So, if you purchase property in a city where rent increases at a slower pace than inflation, the amount of goods and services you can buy will decrease over time due to inflation.Here is what I recommend:Purchase in a city that possesses the following characteristics.Significant and sustained population growth.Rapid and sustained appreciationBalance negative cash flow, interest rate buydown, and increased down payment to create an acceptable cash flow situation today.Refinance when rates fall to increase cash flow.

I find that automation often adds more complexity and time to a given situation rather than helping you save time.

and we carry insurance to protect from those situations but unfortunately there are horror stories and tragedies that happen in medicine. 

So he's cash flowing well on it, he's acknowledged that my situation will be different so I might need to raise rent.3) I think these are all valid questions, but the owner raised these himself too.

My current situation is that I always flip with other people’s money.