Need min 300k liability on personal and 1m on LLC owned (to cover umbrella requirements) Send me your go to guys or companies. 

Just get a good umbrella insurance policy and use a property manager.

It may have been too simple to be mentioned earlier, but make sure that you get yourself a good umbrella policy.

We have things like EAO insurance(see www.insurancejournal.com/magazines/)and Umbrella insurance(see www.geico.com/information/)BUT you best protection is AVOIDING STUPID ACTIONS, as even with an LLC, EAO and Umbrella insurance, you STILL can be sued and loose.

I love the idea of getting a small single family in an outdoor recreational area i love to spend time in where i can rent it out when im not there. but it doesnt sound like a smart business decision. what are your thoughts?

From what I've been told, All State will allow me to purchase an umbrella policy if I also have my car insurance under them which will allow me to get the must needed umbrella for extra coverage on top of my landlord policy. 

Because the property has 3 detached houses on one lot (a 2 bed/1 bath, a 1 bed/2 bath and a 1/1), I thought it would make a charming short term rental because guests can have an entire home at an affordable rate with nice shared grounds/outdoor space.

The outdoor restaurants gig was only good for so long and a lot of restaurants may not make it through the winter.

He requoted all of my policies including auto and umbrella. 

They call it the new Woodstock because the are starting to see fast growth in the area due to affordability, outdoor living, and new entertainment in the area.