And figure out a place where someone could put a dresser at least one that's a tall boy type, although most renter type bedroom sets come with a long dresser with a mirror on top.

Lastly regarding insurance, what is your deductible?

The commercial units would need high credit tenants with very strong, long term leases for this to work. 

Last, if anyone lives on Maui and would like to connect I am always looking for like minded individuals to network with, and maybe, do some deals with! 

Given that it was both a rental and a primary residence for 4 years and solely a primary residence for the last 2 years, is my below assessment correct?

If a single deal works out at this scale, the family has problems like estate tax transfer limits ($13M per child) to think through.Further, as long as the funds/deals are separate from one another, the one that does go well instantly makes the syndicator an "expert" in that specific strategy or market, which then attracts the next 500K social media followers. 

If you prioritize debt reduction and long-term financial security, allocating extra funds towards paying off your mortgage can help achieve your goal sooner.

I can share dozens of other stories of various real estate related "surprises" and "adventures" that I have been a part of over the last 13 years as I worked to grow my portfolio from that one duplex to just over 160 rental units today, but I think this post is long enough already!  

Even with prices going up, I still think you can find some great BRRRR deals in Cleveland as long as you act quickly and put strong offers in on the properties as soon as it hits the market since there a lot of other investors looking to do the same thing. 

What I would do is make sure you have a good long period to get a contractor in and you can pull out if gets to high.