REI is a competitive sport: While you are stuck in analysis paralysis, someone else is buying the house.Good Luck!

Some of the players that have made heavy bets on Harvard Square etc. are down here.

For that reason, Madison could be a good bet.  

It turned out he had never managed property before, in fact he had never touch a single peace of real estate in his life, and was a renter with zero experance beyound being a sales rep for sporting goods store.In the process of trying to make the deal work, he said he would be managing the properties, but after a few weeks of owning them,  he realized he had no clue what he was doing. 

Sounds like you've learned a lot this go around and I bet your next deal will be that much better.

My company works with investors who look more at 5/10 year ROI perspective vs cap rate, and from an ROI perspective - as you suggested especially in cities like SF an NYC - there can be substantial ROI despite negative cash flow; or as my team and I term it "betting on property appreciation". 

Our bet is eventually the whole area will change. 

FWIW my old neighbors (young couple) were both dealers at best bet and purchased a home.

We utilize appraisals and co-star to pull this data, but I'd bet some local commercial brokers could help you out.

At this point, its just sport.