The single biggest issue in my way currently is obtaining enough cash, whether it be my own, or through partnerships or family/friend-based lending (which I am very hesitant about to begin with as this could potentially strain relationships unnecessarily when money is involved).

Single family homes are exempt from rent control when privately owned.  

We own and operate a mid size REI and property management company in Marquette Co. (~300 units or so). 

Quote from @Nicholas Dillon: Hey guys,I own 2 LTR properties, plus my primary home that I rent out half of the year while I live in Indonesia with my wife, who is Indonesian.  

Each individual needs to assess their own ability to handle costs over that time frame when cash flow may dry up.

Obviously the end goal is to build my own real estate portfolio, but gotta learn to walk before running and crawling before walking.

My husband talked to his boss to see if he was interested on selling a small vacant house he owned, and we got it!

If there isn't a meetup currently, you can start your own one.

How many properties do the owners actually own themselves?

But there are a MILLION different ways to structure this, and your friend may come back with his own ideas/requests.