If I had to do it all over again I would consider the following:Top 10 Lessons Learned: 1)Location is still everything.  2)Vacation Locations are more susceptible to significant upswings and downturns.  3)Transportation methods are an important consideration 4)No matter what, DO NOT trust ANY of the "current" OTA's (Airbnb, VRBO, etc), they are NOT looking out for your best interests 5)Whether or not you use a management company, prepare to spend more time dealing with them than you initially anticipated, so you might as well self-manage, and it is "doable". 6)View the properties as inventory, not "homes" and be prepared to pivot quickly. 7)Define "guests" for yourself.

Tim, I had the same dilemma when my wife an I had a condo in Boston we needed to sell 2012 to move to Columbus, OH.  

Hi,Im looking to BRRRR in the Boston or Southern NH area.

What's up BP family..I just acquired my first 6 units in the Boston area and I'd like to get a few opinions on whether or not I should remove the dishwashers from the units, and if I should allow tenants to have washer/dryers.

@Chris Roche  That was the Boston South REIA. 

Close to trains and public transportation.  

However, in the Boston area where I currently invest I don’t think I could match this cash flow...Let me know what you think.

Close to Public Transportation, jobs, schools, popular downtown area, restaurants, businesses, parks, bike paths, rec centers, retail, good walkability score.4.

The good:Clean cut, well spoken, has 2 verified sources of income (one is a transportation business he owns) and meets our income qualifications, good payment history for the past 2 years according to credit report, good communication with me, jumped through all of my hoops.The bad:While the past 2 years are "clean"....Chapter 7 Bankruptcy in 2013, Eviction (says he co-signed with a girlfriend), 2 divorces (which led to bankruptcy) and a "failure to operate vehicle with license" on criminal report. 

I grew up outside of Boston and moved to Enfield CT in 2007 to enroll in the night and weekend program at UCONN.