I am currently renting it out on AirBnB and it is getting me $2,000 a month (safe estimate at 14 days occupancy in a month, although current rate is 18days).My question is i want to do some more reno work at my primary residence approximated at $60,000.

I've met the VA's primary residence requirement and I am trying to sort out my next move but I'm feeling stuck. 

Since I've met the primary residence time requirement in my house hack property, can I use the rest of my VA loan to purchase another property to move into and house hack again?

2) Are there any HELOC companies that open Heloc not on primary residence?

We got two HELOCs (a $50k and a $94k) from Fremont Bank last year. 80% LTV on primary residences and 70% on investment properties.

Would we qualify for a conventional loan (20% down, standard interest rate), due to the fact that he will live in one of the units as a primary residence?

What would you do in this situation? I am currently living in a live in flip house with a great interest rate 3.25% with a mortgage around $825 a month, 6 beds 2200 sq ft in an amazing neighborhood next to a top rated...

Thanks for that explanation Matt.

Had some time to chat with my CPA, and she stated the primary requirements for self-employment are the active income (as you have all schooled me on), the income taxes paid for the business (which would flow through my LLC to my personal return), and the self-employment tax that would need to be paid. 

I closed on a cabin in June and then a primary residence in October with Parker - my finances are not straightforward and Parker found a way to make it all work.