Also given this is in a 10-unit building does it matter, as the rent / NOI will be the primary driver for value?

I don’t know why you’d have an oversupply of rental units.

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.

Look at the homes on both sides.BRRR people you could add units.

Investment Info:Large multi-family (5+ units) buy & hold investment.

DSCR requires 15% down for single and 20% down for 2-4 units. 

Both units have tenants living in them and he is giving them the 30 day notice that management will be passed along to me.

I'm looking for advice on how to best outsource bookkeeping for a rental portfolio of 15 - 20  SFR and small MFH units. 

You'd most likely have to look for a commercial unit, which would be more likely to have the card reading accessories you're talking about + they can keep up with the constant use, which residential units aren't designed for.

@Robert MendenhallA couple points:Buying a 2 to 4 unit building with either FHA or VA financing and living in one of the units is a GREAT way to get started with home ownership and investing.