Let's analyze each issue you've mentioned:1) Tenancy Length: besides issues a landlord can't control, like death, sickness, job loss, etc., the actual management of the property & tenant play a large roll in how long tenants stay in their home.

Sometimes it's best to cut your losses and move on.

There are some accumulated passive losses but not much.

Can you sell without a large loss?

What he does not know yet is that selling even with a loss, is not going to be easy either.You don't need to make all your money on your first deal.

But if there is a job loss and can't pay then do the notice and or cash for keys program. 

And for example there was a Crowd Street deal (Nightingle) where the sponsor omitted losses from their claimed track record (and ultimately was fraud...they never even bought the claimed property).And there appeared to be some difficulty or confusion with obtaining the full and complete track record ( including both realized and unrealized deals).

It is widely recognized as a loss leader within the industry and those who are successful normally have a complimentary business such as a brokerage or a construction company that performs complimentary services.

There certainly may be some loss aversion that drove Tyler's choice.  

When an offer came in for 30 cents on the dollar, I decided bail out, so took a 70% loss.