We managed to navigate it, but it was a lesson in the importance of understanding both federal and state regulations.Given your location in Boston, Massachusetts, it's especially pertinent to consult with a qualified intermediary or tax professional familiar with both federal and Massachusetts state laws to ensure a smooth exchange process.

They were a bit older than me and a smooth talker, and he knew everything about contracting... allegedly. .

I thought this is so smooth.

Not everyone has the same priorities - some care about interest rates the most, other care about the points the most, getting the most leverage, closing timeline, reputation, smoothness of the transaction, etc. 

The big one is worth 850k in a class A/B north side Chicago neighborhood and it runs super smooth, never an issue and tenants all on auto pay.

A smooth sea never produced a skilled sailor (Franklin D.

I think another idea is come up with some renderings and a slide deck and go make presentations at the closest senior centers, Rotary and other service clubs, maybe several nearby chambers and see what kind of interest there is. 

Instead we got some smooth sales dude who had hit rock bottom and is now "rich" because he took on debt to do a RIch Dad program years ago.

There is alot to take in at first but once you get a handle on it, it can be smooth sailing mostly. 

So I consider it worth it, assuming it goes smoothly with a good company.