Don't think of it as "devil's advocate" -- it's risk management.I'm also glad that the devil's advocate stuff didn't scare you off.
Identify risks, rank the risks by likelihood of occurrence and severity, determine how risks can be addressed, and use that information to decide if you should proceed.
I know an unfortunate number of people who went into ventures (of various types) without thinking things through first, for them things ended badly, including a few bankruptcies. The ones that planned things out generally had good outcomes.
My expectation is that @Ty520 has a great opportunity here.