I, since I was young, had this bug and desire that I could not erase to study medicine.The analytical side of me says the opportunity cost monetarily, mentally, and physically to go through pre-med, med school, residency - it is ridiculous.

You do a lease / file audit during your DD period in addition to a physical inspection of any many units as possible (ideally 100%).

A physical asset that is reliable and with positive returns.

Had I never done it, I never would have known until more damage would have happened (physically and financially).

Typically your lender will schedule a series of inspections, (physical, environmental, etc) they'll have a few that they have worked with in the past.

Most carriers see this as an increase in exposure (both from a physical property damage and liability point of view). 

On one hand, it would be nice to have "boots on the ground" and have a partner at the physical location. it would also be nice to be able to afford more and have more options as well as more risk security having more "investors" involved.On the other hand, there would be more people involved so it could be harder to come to decisions and could sour relationships(since it is my brother) if something happened.

One such application is tokenizing physical assets using blockchain technology.

I go to a casino on Monday and roll the dice with no success.

With syndication, investors can enter those markets confidently and have success without physically being in said market.