If you're doing a 2nd mortgage on your primary residence to get the cash for down payment on the new Quad, then you're looking at needing to qualify with DTI unless you find a lender who is a DSCR lender and not a traditional conventional loan lender.  

Hey Shun, I have a few S8 tenants in Detroit, but most of my tenants are "cash paying".I'd start by searching the forums here for "section 8" related threads.

Being that the brokerage is small and new, and we are all mostly new agents, I don't have a large, experienced "team" to help find a buyer, so I am pretty much on my own trying to navigate the selling process of this home. 

That makes it twice as hard to make it cash flow.I would look here for a LTR or elsewhere for a STR. 

Research the County Clerk / PVA office for LLC, and individual names that have a bunch of properties listed under their names good way to identify landlords w/ multiple properties.Just a couple of ways to find package deals. #2 is also a good way to find off market deals which is where you can save the most even if it's just buying a house direct from the owner w/o an agent.  

If you dont have a back up plan before you start , you could find yourself in trouble

This is our first shot at a property so we'd really like to get some experience in while also making some of our money back in the cash our refi.

Clearly, I will find a CPA but I'm trying to get ahead of the game and prepare all the things I'll need for tax filing next year. 

Hey Corey, I’d recommend starting with a turnkey cash flow rental.

I understand these numbers can vary depending on financing, market conditions, and other factors, so I’d appreciate any insights based on different scenarios:All-Cash Deal: If this were an all-cash transaction, what multiples or IRR would you consider acceptable or ideal?