It would be a "DSCR" loan in the sense that it would need to debt cover, but not the same formula as the 1-4 units (rent/PITI).

The hired leak detection company states there is no leak, the roof has been replaced as a result, and the crawl space has also been encapsulated.

If you do find a deal and maybe it doesn’t cash flow for the first year or 2 but you can make improvements, raise rents on under market leases, manage property effectively and cover your expenses at least you will have started and can look for better cashflow over time.

Roast my data or give me some advice :)  Sam, I got you covered.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

When I purchased this property, I used my HELOC to cover the 25% down payment.

If you have a high return on equity, then you are more likely to be making high revenue relative to your existing payment, which means you would be more able to cover the higher payment of a cash out refi and would then have cash to deploy. 

I believe that this might be due to a leaking roof but I'm not sure. 

Quote from @Justin Brin:  I forgot to mention that the arbitrage renter is a very experience host with good reviews for many years and with a team in place.So if that arbitrager would pay me 25% over what I make with it as a STR, covers all repairs and maintenance, then maybe. 

We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.