With Chicago's new Express Permit Program, it's a bit easier to get permits for work that would have previously required architectural drawings. 

These contracts are both dated 2019 and appear to be lease agreements for solar equipment that I, nor the mortgage lender, were ever a party to.

I would just excavate a few 2'x2'x2' (or larger if possible) spot footings, w rebar and Simpson hardware,under the house (you will want to take up the floor to make this easier to do).

@Marc Robinson numbers wise they will always appear to work.

It's also easier to figure out all of the pro's and con's a head of time to avoid lost time and money.  

For example "Just get 3 estimates from general contractors.." is a lot easier written than done!!

We would have preferred to work with them within reason to make it a quicker and easier process.

STR-friendly markets make it easier to get started and grow your business, and the lack of state income tax is a huge perk.

My problem is that I have been looking in my hometown because I thought I wanted my first property to be close by to make it easier at first, but I am thinking I need to look in other markets.

Having a lender who believes in you will make your deals 100x easier.