Appraiser's learned a valuable lesson in 2008 when they were accused of being one of the causes of the great recession.

I would suggest that once you are done reading that book - give it about a week and read it again. 

This is critical to understand if they will be a headache to deal with.

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

Your tenants should have this responsibility.

 try one of those online sources like prosper etc. 

Answering your question is hard as this is a pretty broad question.Sourcing deals. 

This aligns with my interest in passive income.

I'd work on a strategy that returns my capital guaranteed. build to rent direct with ground up developer does this.

Is this how it works, wanted to know from people who have their star’s managed my property management company?