You first need to find a good value add play (given recent legislation, adding inlaw units is now a new twist on that).  

I've tried to gently prod him to consider what may come up, but alas he does not quite get it.

Now that my overactive mind has had a chance to relax after getting all of that ^^ out after a couple of intense days of twisting and turning ideas and insomnia, I'm realizing that while the whole TIC + 121 + 1031 exercise was helpful in that it brought us to a spot where we came up with the idea for how to take the $500k cap gains exclusion from the sale of just the upper, I see now that the whole 1031 motivation that inspired all of this thinking isn't actually necessary/beneficial.

In the end the truth will come out so no need to mislead them from the start, they will appreciate the honesty.With cold calling I have found that a soft and gentle approach quickly extinguishes an irritated call recipient. 

My name is Brandy and I am a noob :) Please be gentle

It's just a gentle reminder of the potential negative consequences.

We bought our first house in England, and got a gentle fixer. 

Dangle the full security deposit and encourage them gently.

To throw another twist into the mix, $40,000 is owed to Medicare, which is going to have to come from the proceeds of the sale. 

But new questions and twists are coming up with every deal.