I would start by talking to the renters to gauge interest before crunching the numbers and moving forward.You could also convert the space into indoor storage.

Thanks for the space and I appreciate any and all help the community continues to provides me as I embark on this new adventure! 

Economists credit a mix of factors including ultra-low mortgage rates, increasing demand for space, and an emerging home-buying demographic: millennials.

@Cynthia Pochatek did they give a reason they would not renew...We use American Modern for non-conforming or high risk properties ...one-off stuff...I think the bottom line is that you can get insurance from any carrier you want for the right price

There is definitely enough space to build something larger (multifamily), but it probably isn't zone for that.

I've been following commercial real estate for the past few years and I've developed a personal preference for the STNL space.

Looking for advice in regards to planning, design, financing (Boston offers loans you do not need to pay back unless you sell the property - if you qualify), construction etc.If you have been through the process and successfully converted extra space into an ADU I would love to chat.

Too much hassle. there are very few banks that will do an actual fix and flip loan and unless your a premier client of the bank the rate will be higher think 6 to 8% apr IF you can get them to loan on fix and flip which I am quite certain 95% of borrowers and a 100% of new investor / flippers cannot get. this is why HML companies have sky rocketed the banks left this space in the GFC and have not returned.. unless of course your a 1% er.. 

Am I thinking about this wrong or does it make sense to take this area and turn it into another 300-400 sqft of indoor livable space?

Repairs and improvements included side porch addition + converting/adding addt’l 400 sq ft from garage to rec space @ $60k.