We should be in shape middle of 2018 to really scale if we want, taking on multiple new equity properties and some major project(s) simultaneously. 

The lender can have 3 files going, and do everything simultaneously.

You cannot simultaneously provide housing support to your son, to qualify him as your dependent, and then reverse this fact on another page of your tax return claiming the same money as income coming to you.

It could get overwhelming unless you are really super excited about doing it simultaneously.   

You might be able to get a mortgage broker to qualify you for a primary and an investment property simultaneously *if* you have sufficient income, ratios, credit score, down payment, etc.

It's fine to not account for the cost of property management if you want to go that route, but keep in mind that you're simultaneously saying that any time you spend on this property (marketing, screening, repairs, etc.) is worth $0.00.

I figure over ten years I'll be able to purchase five properties with 25% down while simultaneously getting a cash out refinance on those five properties to buy five more.

I am looking to do a cash out refinance, so that I can simultaneously lower my interest rate on the note and pull cash out.

He also talked a lot about the value add possibilities of changing traffic flow, attracting certain tenants, upgrading facades, considering synergy (Churches draw crowds on Sunday mornings, Restaurants draw crowds on Friday and Saturday nights, so a parking lot need not accommodate max crowds at both simultaneously... etc.

Along with that, I like what your inner voice is saying, and you could be doing all of that simultaneously.