Do you know of any cases where a umbrella policy has paid of a claim?

For a Buy & Hold, I would suggest an Umbrella policy, 2-5Mil, depending upon number of doors. 

Do I go with the basic plan, or should I add loss of rents and possibly an umbrella policy?

They make it easy to package together small or large portfolios and get one big umbrella mortgage on them.  

I still plan on getting an umbrella insurance policy for both properties for protection there and i figure any Possible LLC liability protection is good idea as well

Someone who specializes in rentals, fix/flips, multifamily properties (quad/duplexes) and umbrella policies for LLCs.  

And then a 3rd umbrella LLC which owns the 2 other LLCs.

I own a few properties and just use a good umbrella policy for asset protection.Good luck!

Your business entities need to be insured as well.Consider, also, that if you own everything your own name (no business entity structure) and your umbrella insurance policy has to pay out, it means litigation was brought and you lost.

I would also follow it up with an umbrella policy for between 1-6 million dollars.