Personally, I love anything by Robert Kiyosaki, with "Rich Dad Poor Dad" being the first of his books that I read.

I have 50k in equity built up and am looking to buy my first rental property, most likely a single family house.

Then I will rent out the entire house the next year.Could you please recommend someone I can contact to get an insurance quote? 

What I would do is tell them you sold it and person moving in once mom moves out. they will never know that you did not sell it. 

My insurance company won’t let me rent my 2 car garage or an office space that I have because it poses a “threat” of a non-tenant person coming onto the property and potentially posing harm to my residential tenants.

I personally have nothing but nightmare and horror stories, not necessarily problems with the tenants, just problems with the procedures and the paperwork, poor communication from the HUD caseworker etc... 

My question is how long do you personally wait to see how your Airbnb venture is going to go until strongly contemplating long term?

Quote from @John Su: The tenant is normally responsible for snow removal, just like the owner of a house.

Personally, I do not believe these fees are in the best interest of the owner and we do not charge mark ups on maintenance.

If this is a very angry person you might also consult a lawyer on your options should they threaten you personally.