I wouldnt sell either, personally, but it is apparent that he just has no interest in holding onto the property since it was more of an incedental investment than a deliberate one and he has a career that he enjoys very much instead.

You do have to be careful as I have had some realtors do something similar by using properties in a comp (whether in error or deliberately) that had the effect of skewing and inflating the value substantially.

Essentially, this one IRS auditor uncovered a vast tax dodge where the grandparents were running several million dollars through shell corporations set up and owned by children and grand children, paying zero taxes along the way with deliberate obfuscations, magic hand waving and smoke.  

I've deliberately avoided Aurora because it's a bit too far for me to personally manage at this point, but I know you'll find something great there. 

For education, you are in the right place with BP and local REI meetups where you can find local mentors would help too ... for experience, you'll need to get in there and invest, but do so intelligently and deliberately.  

Doing so could cause the IRA to be considered distributed and incurred lots of taxes and penalties.I want to avoid that.I am thinking about deliberately setting up an arbitrage situation where I rent the real estate for 40% of the AirDNA revenue with a 10% of sales kicker to an experienced 5-star STR host.

This is when negligence or deliberate damage occurs. 

Begin with your goal in mind and you’ll begin taking deliberate steps to achieve that goal.

I know the seller themselves could provide information but I am concerned that motivated sellers will deliberately leave out the bad details of the property.

If the scenario was that they admit to poorly estimating the job, then I’d guess they deliberately low balled it to get the job.