From what I have deduced from your response, there is no need for overcomplexity as long as I do not pierce the corporate veil. 

I retired from a corporate real estate gig at a Fortune 500 so I've dealt with many professionals through the years. 

This loss could reduce your taxable income on a dollar-for-dollar basis, especially if your Modified Adjusted Gross Income (MAGI) is under $150K.However, the debt must be bona fide and a real, enforceable obligation.

Although this is technically inaccurate (I saw a case where a sheriff sale of this sort was challenged and the challenge lawsuit took 11 months, deed recording came after that), that is the typical practical waiting period to get the title insurance for the resale.Whatever the mortgage balance, that’s now your obligation to get paid off; before even bidding on any sheriff sale property you should have a good idea of any remaining mortgage balance(s).

I am getting older and really don't want to live the corporate life anymore. 

This makes it seem like you are obligated to keep this tenant if they want to stay. 

Issuing a subpoena to a trust, a corporation or an individual has NOTHING to do with “piercing the veil”.  

How long will he be employed if he is on podcasts presenting data about how much Airbnb is hurting communities and the housing market.That being said, I think Airbnb, like corporate landlords, are easy targets to blame, even though they certainly add to the problem, but are not the problem.  

From my understanding, I will need to have the complete the title and municipal lien searches, correct my title to reflect me as a single owner based on rights of survivorship acquisition and complete all other seller side obligations a title company would handle. 

Seller Default: If the seller defaults on their obligations, the buyer may face challenges in recovering their investment.