If anyone is familiar with massachusetts, the areas vary widely- cape cod, new bedford, taunton, south shore, and of course boston itself (out of my league d/t price) are all much different in price/rent ratio, schools, crime, etc... what are the things that matter most to you and influence your decisions when looking into different markets?

That cost may influence your decision on what to do with the property.

Are you involved i.e. what is your sphere of influence?

I would also say that your investment strategy will be influenced by the market in which you invest.

Would you choose to live in the top or bottom and what factors would influence your decision?

@Grant Rothenburger, I don't think it's necessarily a lack of deals, but that everyone mailing to the same Absentee Owners.Investors in overcrowded markets need to look at alternatives like Seniors who have owned their home for 20+ years or Homeowners with low Financial Stability Scores (FSS).There's even a new list where you can mail to the children of the elderly homeowner - since they are the influencers.

You haven't revealed anything that would alarm a seller at this point.Get a redacted set of financials to share with qualified individuals.Have an NDA ready to go.No showings or deep due diligence without an LOI and earnest.Locate COIs (centers of influence) rather than marketing to the masses. 

One thing that just hit me today is: how much property taxes* might influence your return on investment.

I am going to start pulling expired listings or soon to expire, find the FSBO and try to influence them to let me list for them.

Those traditional homeowner purchases are where I'm putting in my marketing efforts currently with SEO, reaching out to my sphere of influence, door hangers, talking with neighbors and anyone I'm in front of, etc.