Before anything I would make one adjustment, which is to live in your first property for two years instead of one: this way you qualify for the capital gain exclusion on primary residence for the next 5 years.I grew up in Metrowest (essentially the areas you mentioned) and yea, it wont be easy.

I was researching strategies and attempting to formulate a solid way to diversify my future portfolio against market risk (and adjust to take advantage of opportunities).

The adjuster from my insurance company suggested the units underneath me to file claims using THEIR insurance policies since they need to prove I am liable for the leakage (due to negligence). 

Then adjust my offer to make around 10-12% ROI. 

I am already seeing longer days on market and price adjustments through many cities in my target markets.

For example, in cold climates, utility bills are higher in the winter than in the summer.

For example, in cold climates, utility bills are higher in the winter than in the summer.

Appraisers know the value adjustments for rehabbed verses not.

With COVID-19 that may need to be adjusted.

For the self storage part of the inspection, he primarily focused on the roofs, HVAC (in the climate controlled units), and the drainage and asphalt.