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. 

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. 

I have the opportunity to list sell multiple acres of virgin waterfront property in Trinidad and Tobago.So I'm looking for potential investors as well.Which islands do your company typically operate?

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

If you scroll through zillow you will quickly see multiples of these designs.

Quote from @Kara Matson: I'm a first time homebuyer trying to add multiple touches to my starter home.

From that perspective, this is a pretty nice exchange.

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.

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.

9) adding multiple ADUs or adding an ADU to a quad looses F/F conventional financing.