So, the actual increase to market rent will be much lower.

That will be tough to use your HELOCs together to get another loan because of your collective DTI so it will depend on that.

He has been alongside me on the other deals so I’d like to give him equity/skin in the game and I don’t know how else to do itQuote from @Basit Siddiqi: Getting a property with a partner / friend will not help you from getting hosed on taxes.I wouldn't move forward - You mentioned beng a high income earner so your hourly rate is very high.

While I will still lose money on it in the long run, I'm at least breaking even on it monthly and no longer have the headache of it. 

I will back it up with sound logic.  

At least ones that will walk the property with you and give you an fair estimate. 

Going to a lender saying "I need $150k for rehab" will only lead to potential scam artist lenders.

While people will share a bathroom in say a 2/1 it is likely a harder sell in a 5/2 and the price you command is less. 

Despite if it works and or what anyone says... arbitrage will always  have a special place in my heart since it was what got me started in this RE game. 

@Jordan Miller most Class A & B rental properties bought since 2021 really don't cashflow from day one.Class B will take 1-3 years to start showing cashflow.Class A, 3-5 years.Current investors keep making the mistake of looking back at deals from 5-10 years ago when prices & interest rates were both a lot lower, but NOT rental rates.