My hesitation is  mostly sentimental and it's a great rental.

He's also pretty set on staying for sentimental reasons and wanting to pay a cheaper rent than the monthly mortgage.

I've done the BRRR calculations and it makes sense for a lot of reasons (sentimental and financially) that I should take over the place.

I am not too caught up on making sure it positively cash flows while I'm living in it either.I know a few of these questions will be better answered by an insurance agent but I'm curious about general sentiment from investors who have spent time dealing with homes in a flood zone and get a feel for the thought process I should be adopting when it comes to looking at this issue.Thanks in advance!

I share the same sentiments with the above responses. 

I could be wrong but that is the general sentiment I have heard.

For personal sentimental reasons I do not like to see this property go at any price much less than for a steal.The property with the house on it I think may be prime for a year round vacation rental so I want to get around to crunching the numbers on that possible play but she is greatly adverse to any ideas of renting as she has had bad experiences with that in the past and is too much stress on her so in order to do something like that I would have to buy it myself, or with partners, so it is 100% no longer her problem or concern. 

.…. with current negative market sentiment adds another layer of risk.I started developing with a small build, project was 3 villas. 

There is a specific property that I would like to purchase if it ever goes on the market for sentimental reasons...  

Unless it’s your parents or somebody motivated by some sentimental reason it won’t happen.