That just seems like an awkward situation, to pay yourself out of someone else's account.  

I'm in an awkward frame of mind. 

Unfortunately, it sounds like an awkward situation for you. 

I know this is all part of the job and I understand all the reasons people vacate but I'm still left with the awkward situation of having to make judgment calls.

They can say no, it gets awkward. 

I just feel awkward sending them the bill right now.

It just gets way too awkward. 

I haven't observed the kind of hand-wringing and awkward conversations typically associated with massive layoffs and job scarcity in the O&G sector.

Pull the tax record for his lot, get the name, run it down on the local county crime records and do some Google searches for new stories with his name... beyond that, generally agree with Splitrock's assessment here... between him and a renter, the renter is the least invested in staying in place in a socially awkward situation, so they'll likely move way before he would.assumed county for the search... http://justice.peoriacounty.org/Search.aspx?

That would be the most common way to partner up but stay 1031 compliant.Since tenants in common can be awkward, after the 1031 is over it is possible to take each tic interest and contribute it into a new entity in exchange for membership interest in the entity.