I would just get clear on your goals and make sure you have the time in the 6 months to put the lessons learned into action.I would also be happy to connect if you want to know more. 

They/you can't choose the carrier - their software assigns it.Fortegra is one of the carriers (paper in insurance parlance) that their product is written on.That said, Fortegra is A- rated I believe by AM Best so that isn't the issue.I'm going to take a guess and say that your umbrella is written with PersonalUmbrella.com (Markel) and they require all underlying insurance to be A-rated but also with an admitted carrier. 

That can help narrow down the best neighborhoods for your investment goals.

My ultimate goal is to house-hack this deal as well. 

I would have asked you what your long-term goal is but you have already thought about it.

When most US investors are faced with the prospect of converting (lots of) USD to JPY, to buy properties in cash, that in depreciate in value (when contemplating resale) and face decreasing rents over time... you need something else to justify choosing Japan over the US.

I’m passionate about real estate and am working towards building my investment portfolio, with a goal of acquiring five rental properties over the next five years.I’m here to connect with like-minded individuals, learn from experienced investors, and share knowledge along the way.

When speaking with them, demonstrate genuine interest in their situation and goals.

For property selection, choosing a duplex or triplex in a good neighborhood can provide steady cash flow, while adding an ADU to a single-family home works well in areas with high rental demand like Portland.

However, rezoning now could still offer some advantages depending on your long-term goals.