My original goal was to buy 5 rentals and have them paid off by the time I retired.  

I'm 33, so I know if I hold something 30 years, it's going to appreciate, and my main goal for investing is equity for retirement funds.

If you plan to retire from everything and live more of a "work-free" life, the path you choose would be good.

Thanks Sean- so as long as I own both the land trust & property mgmt LLC and also meet the material participation requirements then the hours for material participation just retire to the property itself the fact that I am earning the hours while managing the LLC doesn’t matter correct?

My last few years on the "day job" before I retired, the absolute worst part was looking for and hiring employees. 50% or more would not even show up for the interview they scheduled, and wouldn't let you know. 50% of the ones that did show up were such dead wood when they got in there that it was obvious why they were unemployed.

It's a side hustle started aside of my employee job and I feel that this is my best plan to pay my 4 kids college starting in 2027 and secure my dream retirement in about 10 years.

It's just "will we be able to retire early or not?"

My BIG dream is to build a portfolio big enough so that we can replace our current income and retire comfortably (dream big they say, right ;)?)

He's probably retired and/or extended with his son's development,  but he was a hands-on HML meaning he was very knowledgeable and would help underwrite your deal as part of his DD. 

I currently have a CPA (only handles taxes and offers standard tax deductions advice) and a wealth manager at Abacus (handles retirement investments and stocks- IRA, 401K, etc).