The biggest trade off I have heard from someone (also not a CPA/tax advisor) that qualifies as REPS is upon sale, you no longer have long term capital gains, but rather active income.  

then u must have an established relationship with them bc most would just cut you out.  

Along with this activity, an operating agreement should be signed, a board of directors/ advisors should be formed, and board meeting should be held along with minute meeting notes being taken.

As a property manager, creating a standard that establishes the trifecta of benefits and tension is good. 

Most likely you will establish a Solo 401(k), due to the additional benefits, some of which were already mentioned.

I have two friends who own rental properties and they are successful with their properties, I read Rich Dad Poor Dad twice along with Rental Property Investing and Power of Habit, I've been told by multiple people apart of the Baby Boomer and Generation X that they wish they invested in Real Estate at my age, I was a Resident Advisor at my University and I enjoyed that role so some of the skills are transferrable, and lastly this is the best time for me to take a risk.

Your advisor is right on in my book.

Of course establishing what the assessed value was 20 years ago is less obvious.

But will just depend on what you are trying to establish.

I am hoping to find an opportunity to help an established Investor with any administrative tasks, social media, or marketing in exchange for a chance to learn.