They have the choice of finding their own insurance or they can be automatically enrolled in my master policy.

What should I look for before making an offer on a property like this?

Japanese people culturally like brand new and shiny products and you will have a small market of investors who won't touch unless you offer attractive yields.

I guess a flat seasonal fee like any insurance policy, sometimes you win, sometimes you lose.

I would encourage you to make the offer that works for you. 

The program is neither good nor bad, there's just different pros & cons compared to cash paying tenants.Have offered to schedule a call with you numerous times to try and assist you, but you seem to prefer posting & posting & posting - which will take so much longer:(What are the chances you'll actually invest someday, given how long it's taking you to do basic research?

While shopping for home insurance, I kept receiving higher premium quotes.

I'm inclined to take an offer and move on.

If I create a debt fund that offers 9% interest on first lien notes with a 5-7 year payout, would that be attractive to high net worth investors?

If there is any advice you have to offer,  I'm all ears.