But this face-to-face interaction enables me to detect if the individual is full of #$%t!.

It enables you to get last minute bookings for a couple looking to get away.

The other scenario you may want to think about is a shorter term rental strategy (Air B&B) or renting mid term to hospital workers/professionals for several months at a time - that may be more lucrative on the income side and enable cash flow, but then again you have the ebbs and flows of how often you can rent it out.

Identify a property that needs work on the MLS and purchase as a primary residence (which enables the best possible financing terms) - move in & make repairs (that can be financed into the loan).

It is easier to work with their marketing and operation standards.You should also be talking to large hotel management companies; which will facilitate your ownership of larger properties, with their proven expertise offered to you, to enable the better hotel franchise companies to give you the higher-end franchise.

My main investments are in 2 Sub S corporations that will not enable the properties to get the benefit of the free stepped up basis. 

Google voice them with "Do not disturb" enabled.

Wouldn't that enable them to do the deal without me?

Just like how the ultra low rates have enabled "too many" people to become homeowners, its created this flood of investors who couldn't invest before to use enhanced cash flow to enable them to invest and attempt to scale.While I haven't read the book you cited, I'm guessing it started with appreciation for wealth generation, then you switch over to larger apartment buildings for cash flow for your retirement. 

The FHA 203k loan program enables borrowers to finance home purchases or refinancing along with renovation costs.