I figure the upside to the rental scenario is, of course, investing in multiple properties, while a downside would be having to most likely get a conventional loan on the second house with 20+% down and proof of sufficient enough financial reserves to handle two mortgages. 

It’s definitely possible to refinance multiple properties under a single loan, often called a portfolio loan, but it depends on the lender.

I cannot qualify for traditional conventional for multiple reasons but the over 200 to 1 debt to income ratio is a primary reason.  

A disadvantage to this type of investment is that it's likely your MOIC (Multiple of Invested Capital) will be lower than that of a common equity investment. 

Looking to hear what you would do - I've heard of people targeting 1031 Investors to sell large portfolios or multiple buildings but have no idea where I would begin outside of asking a community like Bigger Pockets.

If they're in the same state, that will make your legal team more streamlined, but otherwise, you have to form all new vendor teams when assets are scattered across multiple MSAs & states.

I have been able to do this for both purchases and cash-out refinances on multiple deals for clients of mine.Typically your max loan-to-value will be 75-80% LTV, but this specialized program will limit you to 10% LTV/LTC less than what you can traditionally do.

In the end we decide to go with Digb because the also handle the taxes and multiple LLCs really well. 

Any time you have multiple homes on the same property, you're going to have problems getting financing.  

Not sure I will ever do another one with Multiple investors and having to do a PPM.