Does it have enough reserves, any special assessments on the horizon (could be extra thousands in additional fees), when is the next big expense coming (like roof change, elevator replacement, etc), the rent cap and what rents options are available.

I’ll have to pay taxes on the mortgage boot.

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?

@Hamada Beeka, since they have said they won't allow you to move in I would ask that they are offering to pay you.

@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. 

You can only do it in certain zones.Here is where you can read up -https://raleighnc.gov/permits/services/short-term-rentalsAlso, you won't get any extra appreciation over a similar long term rental.

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