I am an ultimate beginner, I have a duplex, that my wife and I are "house hacking" but  I didn't know what I was doing when I bought it, if we rented our side we might brake even.

I want to continue to accumulate properties that cash flow (open to looking in different regions, especially Western Mass), begin flipping, and be open minded to all opportunities to build a fluid RE business.  

As these things are always fluid and changing.

If he is very enthusiastic on this, and the money is technically what he has earned/saved, then it may be very difficult for you to put the brakes on this.  

I started looking into real estate about a year ago, but i got laid off so I hit the brakes on doing anything.

How was AHA able to brake the lease after only 7 months?

I was screening a tenant and I couldn't verify previous landlord and the tenant gave me there last bill which had everything they were charge for dented refrigerator, resurface tub and others items along with braking the lease (I was going to approve this person) but I was persistent and finally got in contact with them they just said in writing that they owed money so I denied because of that. 

California is another one of the nation’s strongest real-estate markets:“Southern California home sales crash in warning sign to nation” Southern California home sales hit the brakes in June, falling to the lowest reading for the month in four years.

The one person that really makes or brakes your business is your property manager.

And since HOA dues ALWAYS go up (usually annually), I'd put the brakes on this one.