If all further work must be classified as either a "repair" or "improvement", then that would imply that there can indeed be "repairs" to a property that has not yet been rented in the eyes of the IRS. 

Try one of these two web-links: https://www.countyrecordsresea...http://www.retran.net/I have no affiliation with either company..

Did you try Steadily?

My realtor mentionedan umbrella policy so I’m trying to understand why or when that type of policy makes sense  

If they say yes to every deal you want, they have commission breath and are just trying to get the deal done.

You can also try looking on meetup.com for virtual options. 

Try and see if you can connect to some one who has done thishttps://www.facebook.com/gulfcoastrei/

As the owner of a short term rental property management company, we help owners who are frequently overwhelmed trying to do all of this on their own. 

Like my colleague said - there are some restrictions with trying to obtain another fha loan when you have an existing one in place.  

"Never buy weird if you can help it" is advice I routinely give, and it goes without saying to try and avoid creating a weird place that sticks out from what conforms to the neighborhood.