The terms you will get with an owner occupied loan are infinitely better than what you will get  trying to wrap both properties into a commercial/portfolio loan, that it really wouldnt make sense to wrap them both into the single loan.

I didn't know that much about flipping houses, so I just kept them and grew my net worth and built my real estate portfolio. 

It's worth more than a portfolio.

Family business - call to day,"Until you get up to speed with creative methods of controlling real estate, I would suggest you work with an investor (coach), someone who has a portfolio of residential and commercial properties.

A portfolio lender will likely look at the "global" DTI - that means totaling the personal and LLC income and totaling the personal and LLC debt. 

I could have bought more in there but didn't want to hold much of that in the portfolio.

Hey guys, I have recently started acquiring buy and hold rental properties, and I'm looking to free up cash to grow my portfolio.- Notes: my residence has approx $200k equity and is currently a few years into a 30-year conventional mortgage at 3.25% interest.

As far as my portfolio, would you recommend a flip first?

I have a couple of investment properties and want to expand my portfolio.  

Once I have a good portfolio I can quit my job and focus more on REI.