Remove covid pressures and the underlying figures are still enough to drive interest here - relative job growth, stable state government, beauty/outdoors, proximity to those fleeing the West Coast.If you want to optimize cash-flow and are able to invest in other markets, there are much better alternatives for that.

Hospitable(messaging), Pricelabs(pricing tool), Stayfi(capture guests emails), touchstay(guidebook), ring outdoor camera

What's the difference with having an LLC formed vs. having a large umbrella insurance?

You should also get an umbrella policy and ask about things like if a worker or sub contractor gets hurt on your property how you'e protected.When dealing with contractors always verify their insurance with the carrier not the agent. 

I have my cabin in an LLC and also have a large umbrella policy.

Then all this hassle and headache is for nothing anyway.Chances are you never get sued and continue with all this hassle and headache for nothing and don't even know it.I just carry a large umbrella policy and call it good.

I will set up an LLC where your property is, buy the commercial umbrella as well as landlord policy.  

While the LLC provides asset protection, you can also achieve similar protection results with an umbrella liability policy of sufficient size if the properties are in your personal name.  

My cleaners are phenomenal cleaners but generally stink at really understanding if something breaks (e.g. beach cart, umbrella goes missing, etc....).  

As the theory goes, if you wrap each property in two layers of LLC's in this way, it's very unlikely that your personal assets would be at risk due to a lawsuit relating to your investment properties.However, I've heard a few people on BP prefer to hold properties personally, likely due to easier financing (FHA loan vs. commercial loan) and they cover their risk to their personal assets (due to a lawsuit) with an Umbrella insurance policy.