You don't ever want to double book and have to cancel one of them.And the guest giving a phone number in the first message like in your original post is against the rules and the guest knows it. 

It’s a newly renovated 3-bedroom, 2-bathroom home, just one block from the ski slopes and four blocks from downtown.The current owner has been renting it out for $30,000 per month during the peak winter and summer seasons.

Look for one that has other listings and experience in the area.

What you were able to do- makes a good case for not disclosing all the amenities one provides- publicly.

Wind is one of the subtle items that Insurance companies are starting to exclude. 

The early portion of my career was buying turnkey rentals, like the one you described. 

One of the Keys to Success in Multifamily Partnerships: Communication In the world of multifamily real estate, teamwork is everything.

@Duke Butterfield no one can really answer whether or not real estate is a good choice for you - except YOU!

I have it narrowed down to two agents, one has more general experience in the area and are part of a large organization.  

2) You have one rental now, what's your goal of buying more?