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.

If you build a good relationship with a local realtor, they can assist.

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.

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

Any assistance would be greatly appreciated. 

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.

Currently I'm using propstream, I was having some issues getting my account with batchleads set up and their service hasn't really been the best with assistance.

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

This is something that legal aid might be too able to assist you with if you are not very well healed financially.Good Luck!

I had a response on a previous post this year about what the private lending restrictions will be here --> https://www.biggerpockets.com/forums/22/topics/1174919-bough...Here's a re-post of that information though:------------------------------------I do have a DSCR lender who can assist with a limited recourse loan that will close in the name of a self-directed IRA.