The 'relocation specialist' with the company says the family would need minimum 3 months, and the insurance company would be willing to pay significantly over my asking rent price (I'm asking for $2000/month and they will pay $2600.

@Leo GregoireTo answer your question directly about cash for keys:In rent-controlled states like California, you can sometimes pay 10 to 20 grand a door to get them out.I have never had to go this route before.

Why do you need to pay for a skip tracing service to access property phone numbers?

@Vi HuangNever heard of them but there are way too many lenders out there to be paying fees to review the loan.

Plus they would have to pay a mover. 

Most owners don't want to pay a PMC enough.

Any buyer willing to pay a $10k assignment fee up front is going to close. 

My water company only pays a visit if you're not using water.

And, a minority of landlords will experience tenants who stay put for years or decades paying under market rent.

There are great tenants willing to pay market rate.