In any event, I would be glad to assist in any way I can as I have been through what you are likely about to go through. 

If you are looking to work with a STR focused realtor that probably has the most STR sales in the area, is an STR investor himself, has a STR property management company and assists with staging if needed, and can give you a true pulse on the market, I recommend reaching out to @Josh Green.

Offer to be his/her assistant for free, do all the stuff he/she hates doing, and learn the business from them.

Random things like this.I can only imagine if they did allow you to add all the bedrooms, they would make you also add fire sprinkler system and a commercial fire alarm system like residential assisted living. 

While showing one of the newly vacated units to a potential renter, he informed me that he was displaced because of the hurricanes, and that FEMA was providing him with assistance for moving, including paying his security deposit, rent, and moving costs.

In terms of the second scenario, the upside I see is the option to get a different kind of loan (say, FHA with a lower down payment and other assistance programs for K-12 educators like me) since I'd be getting a new primary residence instead of a second home.

I am happy to assist and have a detailed discussion to go over potential options to help if you would be open to it.

In Illinois, the minimum age to officially become an unlicensed assistant is 18.

Hi Sushil,My firm does portfolio loans, and if you fit the criteria, we may be able to assist.

I rent STR mostly through airbnb which acts as a rental manager and I have an assistant that I personally hired to flip/clean the units and also on site for renovations.