Look for any evidence of an oil tank on the property.

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

The heating is oil and the owner says he installed an electric hot water heater, but the basement was in such disrepair that we could not get down to see it.

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. 

I'm currently learning about conveyances and disclosures, specifically the Natural Hazards Disclosure Statement.  

It's the nature of the beast, someone is doing a job and they want to get paid for it.