Are there specific factors you look for in an area to make sure it’s a good fit for this type of rental setup?

Would you share 3 specific things I should do during my "training period" (if it includes a book, which one)?

Each path has a specific strategy for becoming a specialist in it.You want to be a specialist.

Consult you insurance broker for specifics but I found this policy to be very protective and reasonably priced.With regards to an umbrella policy they are typically good to have.  

I am just starting out with a STR and found that VRBO is not very specific if they are collecting the tax and paying it to the State as a marketplace facilitator or am I responsible for this tax collection and payment ?

Do you think he read this thread and was talking about @James Wise specifically? 

Understand this is market specific. 

@Aishan Gonaduwage what specifically have you read, and how OLD was it, about Detroit being on the decline?

You need to provide a bit more specifics about the property, about the insights you want, etc.  

@Tom OchiengI would reach out to a real estate attorney for specific advice on this situation since you already have one tenant who is being difficult.On a side note, when I have inherited tenants, I have been most successful when I have provided longer non-renewal notices, like 60-90 days, and offered to assist with moving costs.