Can the rent be raised to enable cash flow? 

I was tired of renting and had heard about how house-hacking can totally change your financial status and enable financial freedom, so I set out to find a house-hack.

UPDATED STRATEGYBased on input thus far, here is my updated strategy:Use cash and a construction loan (if needed) to build and rent a 4th conventional unitRefi at conventional rates (original mortgage + construction loan + up to $900K cash out for a 4-plex)Build and rent 2 ADUs using cash outBuild and rent basement ADU with HELOC, construction loan, or cash outStart an ADU building business (there are at least 1,000 homeowners like me in Berkeley - I will meet each one) BRRRR small properties or syndications to cut my teeth with any remaining cash outConsider whether selling or exchanging makes sense once all rents are seasonedUse accumulated cash flow to buy smaller properties or syndications to establish teams in key citiesKeep my eyes peeled for jumbo cash out loans to enable much larger RE investments down the roadShield all RE investments from liability stemming from potential catastrophic losses to highly leveraged triplex in CaliforniaLastly, it will take a while but I intend to report back with successes and lessons learned as I move down my bucket list.  

Those bidders that did not win are the losers, that enabled you to be the winner.Why are those bidders losers?

That's not a crutch that will enable you to hobble to success.

I only bought to sell for a profit, eventually enabling me to buy nicer properties closer to home.

Any sponsor that can get agency financing with 10+ yr rate lock is able to mitigate their downside risk and enable the asset to cash flow through a buyers market. 

It enabled us to leverage our situation and pay for schooling, which neither of us would have been able to do without this investment.

It’s guiding our investments because we actually set a target ($100,000 passive income as a couple in the short term and $150K+ in the long term) and are currently building the seed capital that will enable us to hit those targets. 

Otherwise I am going to sell my current home which will enable me to get a house.