We've been searching sites like LoopNet, for example, but haven't really found anything that's caught our attention.

Our first ( and only ) purchase was a rowhouse converted into 4 units and needing some attention. 

Readers are advised to seek professional advice.

Pay particular attention to adjoining neighborhoods as they are a sign of which direction your target neighborhoods might be heading in.There really is no substitute for actually driving a city. 

Hey, I always come across wholesalers who throw away old/ dead leads. You need to think outside the box and maybe you can close them using another creative strategy - win-win - cha-ching!Also, if you hesitate to call ...

Any pitfalls that I'm not paying attention to?

I provided that detail so that the reader could get a picture of it since it’s a desirable area.

Im the poor step child in this scenario who got lucky to finally get some attention.

The prices around Boston are a little out of my wheelhouse so I've started turning my attention West. 

@Alan Howard -  I think Quiet enjoyment is the main thing you need  to pay attention to here.