Aside from allowing 35 non-accredited investors (or 3.5M if they all invested 100k) what is so much easier about filing for a 506(b) that the long time proven operator prefers?

As far as the first paragraph is concerned, I can't do Convential Loans in TN...only commercial-style rentals, so I will leave that first paragraph to someone local to you.

Remember that a broken hot water heater costs about the same to replace no mater what your rent is. So

As far as property taxes go.

as far as i know, there is no app to 'order a gut rehab for Saturday.'  

The housing price is so high compare to the rent. 

That may be, but Chicago and Cook county are EXTREMELY tenant-friendly hell holes as far as landlords are concerned.Don’t move to a place because of its laws.

Income is a basic requirement for any kind of Conventional/traditional loan.As far as rates, pretty much any 30yr residential investment property mortgage anywhere near par at 85% LTV is going to be north of 7%.

We've had really good bang for buck value with Zumper as far as ILS goes.We also bought a matterport camera and create a virtual tour of each available rental which creates a nice interactive way for prospective tenants to see a space and get an idea for its layout before touring.We use Appfolio for management software and it pushes the listings automatically out to any ILS who will listen which has been a huge help not having to list the same property on multiple sites. 

We didn't have to go so far as to use ozone, as once the above was done, the odor had disappeared nearly entirely.Best of luck with it!