There are any number of Real Estate schools available to you, so choose the one that compliments your learning style, whether that be online or in person or a hybrid. 

First time on this forum, and just introduced through two books I just read by David Greene and Brandon Turner.  

Can I advertise here on BP or is this going to get me banned?

Here's some online software options that you commonly see recommended on BiggerPockets.

Most, if not all are in older neighborhoods without a HOA and on the bus line. 

Turnovers have gone from 2k on average to 4k or more. 

Cities and communities are also cracking down on people using homes for this.

My thought is to take a compiled list of property addresses saved in Excel and then run data scrape from Zillow and Redfin on each of those addresses, pulling the property details back into excel and into the appropriate table I have set up. 

I don’t place all the blame on him, as I understand Massachusetts law is heavily tilted in favor of tenants.

They should be bale to guide you more based on what you are looking for in the area.