Something like umbrella policy or rentals held in LLC or corporation.  

One mechanism of asset protection is an umbrella insurance.  

Similarly, there are tax reporting requirements for trusts, depending on the type of trust, and the state you're in.As I mentioned, I use insurance, umbrella insurance, to mitigate risks for my businesses and rentals.

And make sure to account for the following expenses:1) Mortgage2) Mortgage insurance (PMI or MIP) or FHA Risk base3) Property Taxes4) City Taxes5) HOA (Home Owner’s Association) Dues and Fees and Assessments6) Insurance   a) Property Hazard Insurance (0.3-0.45%)   b) Flood Insurance   c) Earthquake Insurance   d) Umbrella Insurance7) Vacancy Rate (usually 8% - the equivalent to one month a year, or 5-6% if multifamily and/or if experienced, if not use 8%)8) Utilities (you’ll have these if your tenant is not covering them and/or during vacancy)   a) Water § Sewer § Garbage   b) Electricity   c) Natural Gas   d) Propane9) General Maintenance (usually 5%)   a) Upkeep § Landscaping   b) Snow removal   c) Repairs   d) New Appliances   e) Make ready10) Capital Expenditures (usually 5%, higher is the property is old and obsolete, less if fully rehabbed and all mechanicals and roof are new)11) Property Management (8%, even if you self manage, your time still has value and there might be a time when you'll want to be completely hands off or you'll not be able to do it, vacation, retirement, etc.), including...  

I am planning to get umbrella policy that covers my personal assets as well as rental.

Contacting organizations and getting a contract / lease signed for them to use the house, who pays utilities, would I need more than just my standard $1M in liability and my personal $2M umbrella policies that I use on my other rentals, how the amount of rent would be calculated, the going rates in the area you are in?...

I still am not sure what to do with expenses such as umbrella insurance for all the houses.

DISCLAIMER: I am NOT a lawyer but my understanding is LLC's only offer one "layer" of protection and honestly a good insurance policy/commercial insurance policy with an umbrella liability policy will do you more good than an LLC will.

There's now also a patio table, umbrella, and a couple of chairs in the yard.

As a side note, during this process I learned that if I choose to insure a property through a company other than the one I currently use exclusively (for home, fire, car, etc), they will cancel my umbrella policy.