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. 

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

As I advise my potential starry eyed borrowers - I can lend money but you will need extra money for:- Money down for the purchase deposit, you (or your motivated seller/investors/relatives) WILL have skin in the game,- closing costs (including appraisal, title, insurance, fees and points.)- loan carry costs for the duration of rehab/flip or stabilization.

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

Given the costly nature of investments or expenses such as this, in theory your DSCR could take a hit.