To echo the sentiments of other BPers, the transition of my mindset after reading this book is what really made the impact.

I figured it was a sentimental thing.

As a newbie also looking in the Boston area, I would agree with the general sentiment that the key is to catch on to a formerly B/C neighborhood right before it starts to jump in value.

I made the concession to give up some pretty sentimental family property in exchange for family cohesiveness.  

We share your sentiment and excited outcome!

Your post didn't give any visibility to your having done any of your own research beyond seeing a lot of properties for sale, so I would certainly echo the sentiment that you should put in some deeper investigation.

I tend to agree with the sentiment that you don't need a wealth advisor (and I am one!).

If these are things your CPA is unfamiliar with, I would echo some of the sentiments that you may want to find a different CPA or one that is more focused on real estate investments. 

My sentiments exactly!

So the filter is no longer market sentiment, but the actual financial barrier entry.Josh Dorkin has been hammering cash flow as the main criteria, if not the only criteria, based on his own experiences in CA.