Not saying I wouldn’t buy rat holes down the road, but if it cash flows and it appreciates why put all that extra cash into the property?

My cash flow, albeit smaller is 100% FREE to me, as I have no money invested to earn it, and I still have my original investment which I can use to repeat the process. the return on investment for a 100K house that makes 1000/month is 12%but a 100K house with a 100K mortgage that makes $200/month is infinite. also, when your house is paid off you have  terrible return on equity, it's important for us to all maximize what resources we have in all areas.

What's the P/E ratio, how's the earnings per share growth looking, dividend percentage, what's the federal reserve doing?

I’d try to get a technical high paying job and dump my extra w2 money into real estate deals instead

Think about what YOU would do with your free time and extra money and go from there. 

Its a good way to gain a strong knowledge base, expand your contact list and you can still earn some cash in the meantime. 

Should we cash out refinance out primary residence to pull more cash out or should we just use own cash reserve+ HELOC for next down payment and any extra fees?

It may sound nice to pay a 5% management fee but the extra fees can add up to be more than the other company that charges 10% with no add-on fees.

I'd be content with the house being no extra expense to me, managed by a property manager, and just letting tenants pay off the mortgage. 

Usually LLC's are if you buy outright or have a well established LLC that has proof of earnings.