Since I can't change the structure of how RE works in the US, I feel like all I can do is to find a way to conform to it the best way possible so I can mitigate as much risk as possible while also trying to reap the best results possible.

WAY less work, for the same reward (assuming all things are equal) As s result we have shifted our portfolio around so that we have less units now, more cash and cash flow, and are in a much better place to be in the path of appreciation. (3bed 2 bath homes) rather than ODD non conforming triplexes)  In our area a GREAT deal on a house cash-flows just as good as the triplex with way less work. rant over

Truism #1: RE Agents hate Zillow and will tell you to ignore them I find Zillow zestimates reasonably accurate in dense urban neighborhoods, with conforming structures.

It will also conform around all the imperfections in the underneath surface and show them, and look terrible, if you don't scrape it smooth.  

Max entitlement for a VA loan is usually $424K because that's what the FHFA considers a "conforming loan". 

It is possible you are under a non-conforming use (typically referred to as the grandfather clause) and you are okay. 

I broker as well as direct lend.Which has better interest rate pricing (retail or wholesale) bounces back and forth over time.Currently, retail has the best interest rate pricing for conforming loan amounts across the board, and wholesale for jumbo.Small mom and pop independent mortgage brokering is not economical in the current compliance environment.

Alternatively, you can probably get a conforming 5% down loan on it...

@Manuel AngelesThis is a great strategy to get a good cash-flowing asset for little cash while simultaneously taking advantage of record low interest rates.For conforming loans where you get the owner occupant advantages it's only for 1-4 units.  

Not every lender will let you, but the FHA will let you put as little as 3.5% down on a 1 - 4 unit home you intend to occupy as your primary residence.On a loan under the conforming loan limit of $424,100 most lenders will let you put 3% down with stellar credit.On a loan a high balance conforming loan over $424,100 and under the loan limit of $636,500 most lenders will let you put 5% down.On a loan of more the $636,500 you are in what is considered a jumbo mortgage loan.