It seems that most of the older houses we have looked at have some kind of legal issue.

All sec8 rentals are subject to review and approval by the housing authority issuing the vouched.  

I want to share my experience with Jenny Yi, an STR designer in case others have had similar issues.

I'll send you a DM on a recommendation for a law firm a lot of our clients use.

of course the sale of hurricane damaged houses also confuses the issue (my house had no such damage but is only about 4 blocks from houses that did).

What is as important is that you require the insurance to be issued with you as the landlord as "additionally insured." 

We are both nurse and plan to travel for a good portion of this time, so 'living' in the small 1br or studio apartment for residence purposes will not be a major issue for us since we will rarely be there.

It wasn’t an issue of “underwriting does review a file until it was complete”.

Having a rock solid SOW can prevent many of the issues that arise during any project.

Fort Collins did it since the 1960s and only recently created a law against it because of rent rates.