the way section 8 works is different in every county across the US and I have been diving into the matter myself for an 8 unit I am considering putting into section 8 in St petersburg Florida.. but from my understanding you would ask whatever rent you are hoping to recieve and the tenant will tell you what their TTP or total tenant payment is and the county is responsible for covering the remainder of the lease as long as it is beneath their FMR fair market rent.

QBO even has a function where you are able to automatically categorize certain recurring payments so your bookkeeper has even less to do. 

I'm hoping to connect with a reliable CPA that I can build a relationship with to help me get on track with my tax returns but also someone that can provide sound advice as my business grows.

Regardless of the market you choose, please make sure you have reliable boots on the ground (agent, contractor, handyman, bird dog) to check our potential properties and be able to respond in the event of an emergency. 

The main block I have with multi family (which is the route I had intentionally intended on going ) is that because I already own a single family, I would need to come up with a substantial down payment and multi families around my area are 800k +.

So, if the things covered by the policy would cause you to start missing mortgage payments and eventually lose your property then there is a value and for a landlord who is struggling that may be true.

@Josh RicordHow much of your 20k savings will you use for the down payment + closing costs? 

Out of state can be difficult if you don’t have a reliable team in place.

Get written proof of rent payments for the units, and you could try to get tenant estoppels.

What does a Private Lender get out of loaning out 250k in exchange for 360 payments of 2k per month?