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

PPP - Pre Payment Penalty.

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.

As a result, even if you put your number on the National Do Not Call Registry, that company may call you for up to 18 months after your last purchase or delivery from it, or your last payment to it, unless you ask the company not to call again.

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 +.

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

Just to lower your mortgage payment?

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? 

Demand proof of payment on every unit for the last year.