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

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. 

the Scenario:We have an LLC, 2 long term rentals, 1 short term rental, 1 future short term rental about to undergone renovation. I have a general contractors and interior design license. I’m required to have liability...

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.

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

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.

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.  

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