@Kash Tacke I'm a big fan of ADU's in general especially here in the mid west, yes you could potentially be on the front of the wave, but housing density is the solution to the affordability issue, anytime you are investing with affordability in mind is a great strategy to me, and sound like there are some incentives or at least supporting winds form the local city, that in itself seems like it would be worth at least approaching an architect or contractor to bid up some plans or concepts to take tot he city.  

For me, if a place has the mortgage paid off, I leave it...but that is me. 

If you have 300k  equity its no brainer for me.

Buying with an LLC is a great way to safeguard yourself and your property, highly recommended, however, if you’re purchasing through an LLC that was not formed specifically for the purposes of acquiring your investment property, ensure you own more than 50% as LLCs can get complicated with multiple equal shareholders.

For me TX is over-built.

The committees have never said they'll require a specific form of evidence to show that you've rented the place for at least a couple of nights.

For me, the only thing that works seamlessly is the AppFolio integration, which updates every 6-12 hours without any issues.

Aircover is a mild form of property damage insurance where they MAY cover a guest's damage at their discretion, and you will have to fight for it. 

Their in between 120k-260k for the home I want to buy and rent out but I don't know what the mortgage would be, or how much rent should be for me to even possibly cash flow off of it or even after that how much I'll be purchasing the SFH's for if that's what your asking.

However, it's feasible for me to hold onto this property anyway and fix these issues regardless.And yes, the mini-split has a unit for each room.