This model is very appealing to investors because of one class of shares, which means everyone is treated the same, and the cumulative nature of the pref. 

You might want to think about incorporating and become an employee to your own corp, it might end up working out better for you from a tax perspective.

I plan on leaving my current job in corporate land soon and will be taking with me a decently sized 401k. 

Alternatively, look at Tellus free smartphone app/ PM software which basically incorporates Naborly screening along with tenant maintenance/ communications and free ACH bank payments.

Naturally, I have been telling myself to get my beak wet with a single-family property, first, and then move onto multi-family units.

I'm just not sure if I'm comping apple t apples due to the unique nature of this situation. 

Or do you just familiarize yourself with a home inspection checklist so that it becomes second nature?

For those that don't know I run a huge Property Management company, 1,000's of tenants etc....Running a company of this size there are things that come with the territory such as evictions, telling tenants no & things of that nature.

Not for the purpose of becoming an agent (I'm a software engineer by trade), but rather for the purpose of learning more about the real estate industry, with a view to perhaps starting a business tailored to the industry.I'm currently learning about conveyances and disclosures, specifically the Natural Hazards Disclosure Statement. 

I'm guessing that "non-trivial" could mean anywhere from $5,000 to $500,000 depending on the nature of the problem that the inspector missed.