So far I am only working with a few clients that I have found organically and haven't yet started aggressively reaching out to my sphere of influence or marketing for leads.

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.

@Michael Le : yup, i agree. ideally i would like to go as large as i can go without being fiscally irresponsible and since i am a newbie to this, dont want to bite off more than i can chew.

Most of my home owners are out of state owners who purchased either their future retirement homes or simply liked the tax advantages of owning a vacation home in a state that is fiscally healthy. 

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?

You do need to be very fiscally responsible, as well, as pointed out above.

@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.