Imagine taking the 20% loss for selling as a portfolio and then the 1031 fails for some reason.

I understand that the beneficiaries of the estate didn't want anything to do with operating commercial real estate, so it was just left to fail.

Too many owners fail to do this, then wonder why their expectations aren't being met.

That said, do ask yourself before signing on the bottom line: if this tax strategy fails the IRS scrutiny test - what happens then?

I have whiffed and failed miserably and hit a couple home runs.  

We were in a meeting for about 30 minutes where I went over every little detail and re-assured her there was 0 chance of me failing.

There could be negligence on your part for failing to maintain them.

A deal that has $1800 for expenses is a deal that will fail.

I do commercial and there are good options but the price ranges are much higher than Single Family and the risk (i.e. in retail, ~80% of the business fail in the 1st year) could be higher. 

Or if you tried it and it failed also let me know.