Check with an attorney and/or with a public insurance adjustor because I work with insurance companies frequently and they are notorious for lying to customers to deny claims.

I am a native of the area and can tell you that Jacksonville is a very large city and on all sides of town there are both good and not so good places to invest but the westside is not notorious for the best place to live.

AirDNA is notoriously unreliable when there isn't many comps to add to the algorithm.

Flooding is notoriously common in Chicago basements.

That doesn't fit the BRRR strategy so I can tell you a whole lot about Memphis and why it is a great city, but I don't have the contacts to share with you that are going to truly benefit you without knowing more about locations, price points and ultimately your expected outcomes.It is hard to type all of that in a way that makes sense and I am notorious already for long posts.  

Unlawful detainer attorneys are notorious for being uncompromising and unfair.

And one person affiliated with a notorious OMG who knows a whole lot about real estate!

Small landlords are notorious for not including all of their expenses in their financials.

Denver is notorious in other regards as well for STR and regulations in general.Converting the duplex to an SFR would have more cons than pros in general. and from zoning questions would be a tough thing to do.Definitely, a home with a mother-in-law suite or a separate living space is your best goal.

Notoriously, lenders and CPAs do not understand each others' rules and are often locked in needless conflicts.