Purchase price: $71,000 Cash invested: $19,000 owner occupy doubleSounds like a solid investment!

Examples of general questions are local STR regulations, general expense expectations to run an STR, etc., expectations for the owner, etc.

If you owe the bank 1M, you have a problem, if you owe the bank 50M, the bank has a problem.If your child dies or has a divorce does his spouse become part owner of the properties?  

Main questions should ask about the seller's:- Reasons/Motivations for wanting to sell- Desired timeline to close- Plan's after selling (relocation, reinvesting proceeds, 1031 exchange, etc)- Back-up plan in case they are unable to sell within the desired timeline- Reasons for not already selling to/with a investor or RealtorAdditional questions will depend on the type of seller lead i.e. pre-foreclosure, probate, fsbo, absentee owner, etc.Here is an example of a youtube search you can use to begin finding call recordings.There are 1,000s and you'll find that the best/most effective ones don't even sound like sales calls.

There are many lots for sale here by the owners which can be had for well under $20,000., as opposed to the 50 or 60k that you will pay to Eagle Rock. 

To locate a property owner, you can typically visit your local county recorder's office or the tax assessor's office.

Have seen owners of condo's and co-op's get into trouble running an AIR BNB out of a co-op.

Quote from @Brian Bowen: Is there a good free method or resource to find owner contact information?  

I noticed the house looked like it was being trashed out, so I immediately reached out to the owner.

Property owners in Florida have faced significant challenges with squatters unlawfully occupying their properties.