If I have several options, I would prefer a HELOC with no initial draw requirements (i.e. to establish a literal line of credit that I have no specific short term plans to use), i.e. not something like the better.com HELOC. 

Quote from @Christian Styles: Potentially able to help you find someone but I would need to know specifically where the property is in order to know who to recommend.  

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.  

They are more like an investment club / provide coaching (I am guessing for a fee) but I as a sponsor was told we don’t get any fee or have to provide any kickbackSomeone I know who is a member noted they do not act as investment advisors or provide investment advice nor are paid based on specific investments but I am sure someone can Confirm this I wonder how they get paid then.. ???

So, the first question they usually ask a PMC is about fees - instead of asking about services and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?

Also, nightly stays should be adjusted based on your specific pricing strategy as well (e.g. longer stays further out, shorter as dates get closer or gaps exist).

@Justin Smith wouldn't do it.Why is he willing to sell you this SPECIFIC rental and not another?

As a builder/investor myself some of your estimates seemed a little off to me, but those can be very market specific so its hard to say. 

However I ran a few quotes on Obie Insurance (geared specifically towards landlords) and for only the 4 houses I checked, I am saving 1,5k a year if I switch.

Quote from @Tanner King: Where are the best places or best ways to collect data on specific markets?