However, ideally if we started both with the understanding that collaborations and building the right team in conjunction for planning for our larger future and objectives we'd get to the "freedom" that we are all actually chasing via RE that much faster. 

I am looking for the passive income and financial freedom. 

If your goal is long term cashflow and financial freedom than trading in two depreciating assets for one that appreciates and helps you scale towards that 10k vision in the future seems like the right move towards your goals. 

While it can be tempting to jump right in, the best thing you can do is build up an emergency fund FIRST and then start working towards securing a property.I do this by working two jobs, may not be the most exciting thing to hear but hustling for a few years to achieve financial freedom in the future is worth it.

In cases where I rent a room I just rely on checking they have a professional health care license and a job in the area but that is only because the roommate is my son.  

I did not initially get my license to do transactions for other people (just my sons) but now that I'm in it, I very much enjoy it and I am in a fantastic firm that gives me total flexibility and freedom.

Throughout this journey I hope to meet a mentor(s) who can help me with my vision to own numerous multifamily rentals to create cash flow, financial freedom, and creating a legacy for my family.

The downside is that I give up the freedom to live in whatever neighborhood I want to - I could only afford a handful of neighborhoods further out in the boroughs.

Is this a health care company that will provide housing to their workers or a company in the business of re=renting space that they rent from you. 

My wife and I have been house hacking in NJ for over a decade, happy to help out and share what has gotten us to financial freedom.