House hacking is also an awesome strategy in CA because you get to lock in low property tax rates and it is relatively easy to cash out the equity you build in a primary residence and use it to leverage your next property.  

I'm not necessarily a Massachusetts investor (outside of my primary residence), however, I'm happy to chat or network if there's anything I can help with.

This prop was seized from the previous owner who now resides in prison.

Resid or with the larger multi's. 

Think self employed productive individual that is responsible and has cashflow but is not what the banks call a qualified borrower.  

Also, what are the typical requirements to qualify for the refinance?

We are not in a position to qualify for a conventional loan of this size, but have a solid exit strategy here. 

Your financials are too tight to not have predictable cash flows on this property.You also could lose the home sale exclusion if you convert your former residence to a rental.  

Would you recommend I buy my first property as my primary residence now to gain the experience of home ownership or look to buy an investment property (out of state most likely)? 

I have been considering an IRRRL on my primary residence to drop the rate on my VA Jumbo loan, but received a flyer in the mail today advertising 100% LTV cash out (appraisal and income verification required) with the same rate I have seen on the IRRRL product.