I'm an experienced property manager and agent based in Boston.

So, location, cost of doing business, utility cost, transportation cost, labor cost and the ability to attract qualified employees will be the critical factors.

Both options, look for single-family with good rent potential (proximity to jobs and transportation, low crime, $1700/month zillow rent estimate) and low costs (convert to electric utilities, repair roof and structure).

Some markets appear to be over heated:Home-Flippers Reliance On Leverage Rises To Highest Level In 9 Years Jun 8, 2017 11:15 PM“Home flippers financed an estimated $3.5 billion in purchases for homes flipped during the quarter, up from $3.3 billion in the previous quarter and up from $2.4 billion a year ago to the highest level since the fourth quarter of 2007 — a more than nine-year high.”The explosion in home valuations in urban markets like Brooklyn, Washington D.C. and San Francisco has inspired real-estate speculators to search for the next big score, with the highest percentage of home flips completed with the aid of outside financing occurring in Colorado Springs, Colorado (69.3 percent); Denver, Colorado (54.8 percent); Seattle, Washington (51.6 percent); Boston, Massachusetts (51.3 percent); and Providence, Rhode Island (47.3 percent).Matthew Gardner, chief economist at Windermere Real Estate noted that escalating home prices in Seattle forced flippers to rely on financing their purchases.

It's all relative.If a household is pulling in 400k/yr and their mortgage is 38% of their income... other cost of living items like food, clothing, transportation are still a small(er) percentage of their income.

I went to a private school in the heart of Boston (go Pats!)

Ideally professional, well-versed/experienced and at a fair rate.I'm based out of Boston but I primarily invest in Central/MetroWest MA if it matters.

i am going to post a photo of the .59 sq ft laminate from Home depot I put in my apartment in Boston because the carpet was gross.  

Another driver is transportation.  

My fiancee and I bought at the time a two bed condo in and around boston for 262k.