I learned the hard way how to shut off water and how to winterize.

I do think multfamily would mint more cash flow but pricing is a bit out of current range.

Besides the higher down payments, higher interest rates, and potentially shorter terms on commercial loans (all easy to underwrite with a couple calls to lenders), commercial deals in the 5-20 unit range are not much different than a 4 unit.  

I also own a water restoration and general maintenance business in the area and the amount of STR owners that we have spoken with is insane.  

I learned the hard way how to shut off water and how to winterize.

Market Range for neighborhood is $330-415k. 

Granted this was on plots of land I didn't pay for, and that are already connected to the city's water and sewer, so there's a lot of savings there, but I'm hoping if it turns out to be this good of a deal I can still scoop up land and keep going

Your PM fees for LTR will be more in the 10-12% range, while for STR it is more in the 25-30% range (and don't forget about GET/TAT). 

Roads, water/sewer, city services, heck even just the planning for such is not a simplistic thing for all. 

@Lorenzo LopezPretend a map of Boston is a pool of water.