My plan is to raise capital for the down payment through an investor and create an LLC with my father to get approved for a DSCR loan.

I think the rent would make a good dent in your mortgage payment but you would still be paying some money out of pocket after all expenses.

It is the only guaranteed payment in this high priced rental market.

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.

Then last option would be a "unsecured" personal loan where the bank offers up to $50K for example to pay off and consolidate debts.The 2nd and the personal loan will pay off debts and lower DTI and you might have enough left over for down payment or just use VA 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 +.

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

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

Agents are typically required to show up with the client at the first appointment with the builder - if they miss that, they can often be cut/pushed out of the deal.