If you are confident in the market then it sounds like a classic sfh value add play.

Classic. 

I'm totally baffled why people are snowed into thinking they're"classic" when in the current form (pillowed 3x6) they're been trending for less than 20 years, replacing the standard 4x4s that were in for 60 years before that. 

I think this is a classic example of the need to balance the rights of property owners with the common good.  

Another classic failure to look at trade offs and instead focus on a pathos argument: "look at what this one person did to get around the system, the rule is terrible and we need to get rid of it".

Hello, I am a complete newb to real estate outside of investing in classical REITs. 1: Located in the Boston Area2: Investing goals: Cash flow, looking to invest in residential property to start within daily driving distance from Boston.3: Fun fact..... the photo is old.

its a classic and there are others that build on it.   

So it's a classic optimization problem, you have to find your sweet spot.I used to be all about cash flow when I got started and over the years it became less important, while the potential for appreciation has become more important for me.

I highly recommend you read Howard Marks’s classic Mastering the Market Cycle.  

This is a classic that's very talked about a lot on BiggerPockets: adding bedrooms and find the best use for any property.