He's had two successful flips so far and after this third one he's looking to pay off the HELOC and roll the profits into his future flips.

I sort of believed that RE would always have plenty of opportunities.  

Cash out re-fi's are very difficult given the economy and the fact it has been an election year.

@Tim HoltFrom my experience, house hacking can work well if you focus on minimizing living expenses and setting yourself up for future cash flow.

I had been using Stessa, which I really loved, but it is buggy and the banking connection to Chase was continually breaking, which I needed to re-connect, but when I did that I had to go through 200+ transactions and re-allocate the expenses. 

Then use the extra roommate rent income to pay down your mortgage and look to refi to a lower payment in the future (3-5 years) - so it cashflow when you move out.You could also choose the smaller unit and STR the other unit to generate more cash to pay down your mortgage and refi, so it cashflows when you move out.Bottom line: you'll have to get creative to solve your cashflow challenge!

If you put those same dollars to investment property you get to write it all off.

Its somewhat like a RE license vis a vi a RE broker licenseyou need to start as an MLO  ( mortgage loan officers)  Before you can became a Mortgage Banker  as stated above you need to show experience. 

Currently speaking with a local realtor about the STR zoning issues, insurance issues, and current/future market in Florida. 2025 should be a good time to look for a property there. 1.

You've possibly stated in writing that you (may have) violated several laws ie. working as a property manager w/o the proper licenses etc. 2.