John, not sure if you are familiar with the current STR situation in Huntsville, but the city has shut down STRs that are not zoned correctly and also not permitted. 

House HackFinish the basement as a separate unit (if zoning allows) to rent out while you live there.

There is also some tight zoning and regulation in Whitefish.

We had meetings with him about we our business finances are in the red, not making repairs unless its a non habititable issue or saftey concern.

Drop by your municipality's building, permit, and zoning office. 

Unfortunately many lenders will see this as a red flag and may not take the risk to lend you the rest of the money even if you use stated income program or bank statement program but those are for self employed borrowers who have active income from their business but write off to many expenses that when filling their taxes their net income is really low or sometimes negative.

Has anyone dealt with section 8 renters before and if so what are some red flags that I should keep an eye out for?

Yes, Chicago has strict regulations for short-term rentals, including mandatory registration and zoning restrictions.

Zoning varies, so always check the local regulations for your specific needs.Financing: While cash purchases are common, financing options are available through local banks and credit unions.

Being in Orlando it's one of the more safe areas for hurricanes but make sure you pay attention to flood zones, get flood insurance as necessary in case of flash floods in rivers, and make sure you can get legitimate insurance providers.