@Kevin Collins you are asking for advice and I am taking time out of my day to actually give you a different view point in an attempt to help and assist you but you are upset it doesn't quite conform and confirm your thoughts in the way you expected. 

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

We also assisted to have mngt contribute thousands to the investor as well.

Feel free to reach out if you still want some assistance with the search.

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.

We are happy to assist you with whatever management team you feel is in your best interest.

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

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.

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.

Oh yeah, that's right, all but ZERO help or assistance.