Perhaps he's selling for financial reasons and I could then go back to him explaining that by avoiding some minimal effort such as calling insurance to deal with some issues could cost him big in the long run because when the market is sh*t in the next couple years (if it gets worse) he will have to hire a Realtor and pay 6% to sell it nevermind the fact that his house is at peak value right now (depending on your market but most places hit peak in 2018) and if he decides in a year he wants to sell it will be for less money.There is always an angle with someone you just need to find it, and sometimes yes it is very hard to do so.The worst case scenario is you get your money back and can mark this down as an 'experience' deal

I usually only take $50 for pet deposit (no refundable) First time dealing with this, I will ask tenant to give me proof of documentation for the service dog (making sure she is not playing the service dog trick to avoid the pet deposit)

Some guests on HA request to deal directly to avoid the fees, which I rarely oblige for fear of losing my ranking.

In what ways can recapture be avoided other than a 1031 exchange?

Avoid the "shiny object syndrome" by narrowing down your niche as soon as possible.

We are so going to make this neighborhood look great"If you are trying to avoid any conflict you can always tell him "I appreciate what you are saying but I have to maintain the privacy of the applicants"

Or is this something to avoid all together?

I am not talking about avoiding legitimate lawsuits with this strategy. 

So the mortgage is always satisfied (as long as it is against the property you  are selling).What that leaves you with though is the responsibility to do two things if you want to avoid all taxes. 

The use of a trust to avoid probate is a common estate planning tool.