I think that we have come to the conclusion that instead of dealing with managing an out of state rental ourselves or via a management company, we will just sell and keep everything local until we are more confident in our abilities to do this properly.

From the numbers you provided my conclusion is that you need to get this property at 75-80k.

Yesterday in my morning emails I saw this lovely message for VRBO:Needless to say I have no attempt of getting the guests info.Under "Take Action" among options I could declare this as an error and asked the "standards violation team" to look into it.Didn't hear until mid day, when I decided to call the customer service.Spent almost an hour with the rep whose conclusion was that I have a language in my listing which in a nutshell asks my guests to avoid an instant booking without telling me a bit about themselves: Who they are, where they come from, purpose of visit, etc.  

@Danielle F.I think you may be jumping to conclusions and judging someone based on a conversation .

If you went to visit your property, you could end up like Mussolini did at the conclusion of WW2 in the European theater. 

That and they jump to conclusions because they aren't involved.

while i understand the answer will be different for each investor, I am wondering what questions I should be asking myself so I can come to a rational conclusion. 

Much more flexible coverage terms, single policy, better pricing, etc.In conclusion, don't look for an insurance company, but a commercial broker that will have multiple commercial companies to help you get quotes from.The problem that you run into, and most other growing investors, is the All State agent is not a commercial broker and usually does not have a good connection to a good broker.

I have come to the conclusion that I will invest in rental properties for cash flow in order to own my time in the years to come.

Even now, most syndicators/PE groups are relying on rudimentary data sources/data sets to draw conclusions.