I’m sick to my stomach just speaking of it.

But I also sometimes think owning only 1 property in LA would be less stressful and a more reasonable mortgage payment would improve my quality of life.

I'm not aware of any doctor loan anywhere that allows for use as an investment property; generally speaking, that's not what they are intended for. 

It really depends on location, quality of home features, amount of privacy for renters/members, and competition.

This attracts a higher-quality renter, ensures funds are available to maintain the home, and reduces the risk of major losses.

With regard to your "DST" and as with many highly structured tax vehicles that have a potential "self dealing" quality to them, there are a number of potential potholes you can easily step in along the way (e.g., constructive receipt doctrine, effective control over nominal 3rd party relationships, lack of genuine risk bearing and compliance with transactional terms, etc.).

Strictly analytical speaking you cannot make a financial case for unleveraged investing in real estate.

You are speaking to the wrong folks.

But, that is not always the right answer and you should speak with someone familiar with your personal situation to get advice specific to you.

I have never taken his course, so can't speak to that, but on the surface of a couple Google searches, of the two he seems to actually be involved in real estate a lot more.