For many years I was contacted by the housing office to provide input of my rents, both Section 8 and market rented units and participated in their annual surveys. 

Not that it cant or wont, but unlikely.If OP applies for homestead on a new property, then I personally would not lie during the application about receiving the exemption on the existing property.

I received permits at the end of October and waiting for them to scrap my lot currently.

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

If I act as my own realtor and end up purchasing a property and receive a commission does the broker I'm affiliated with get a piece of that?

The note from the first seller is only $88,600 so you have more than enough equity remaining to place it in second position which leaves $61,400 in equity on the new property or about 4%.The first seller continues to receive payments and has sufficient collateral to cover the note. 

New-home sales hit a seasonally adjusted annual rate of 698,000.

Connect with local wholesalers and investor friendly agents and provide your criteria to start receiving deal flow.

My lawyer has drafted a month to month lease agreement and an annual lease agreement for residential tenants.You guys are going to do awesome, you both will be looking back one day at the memories you made.

I think tax benefits should be secondary to buying something that would work well as a STR.I would recommend you consult a tax professional to see what possible tax benefits you could receive from buying this STR.