@Art Giacosa
yeah, you have a different situation since time expenditure and cost aren't an issue. Normally, I'd recommend looking at the cost benefit to having insurance for all your LLC's since most people would go broke just defending the corporate veil of their LLC's without the insurance company's legal team to step in for you! But, you don't have that problem --- or you don't consider it a problem. Oh, and personally those who see insurance companies not ready to pay to me means they need to understand their coverage better and/or hire a more reputable company.
The board doesn't even have much of any threads about actually being frivously (is that the term/category we are talking about?) sued. Its not even in the news cycle about "ambulance chasing laywers" suing high networth individuals. I only seem to see it here and any investor related "topic."
My main point is to chase down "sampling error" and perhaps confirmation bias. A few years ago, I listed a property and the sellers were asking about if they could get $40l-$50k more than asking --- it was and still is pretty common in my market. I pulled the listings for the past 12 months. Literally half the properties sold for under asking, and half sold over asking. And yes, there were properties that sold for $50k under asking. You don't hear about those --- who is going to go onto facebook and brag about that?
While I agree that I think there is a segment of wealthy individuals who pay good money to keep themselves "hidden" --- whatever they do. I understand the need for privacy. But, there are plenty of wealthy people out there who aren't hiding. Take identity theft.. I've been wondering for nearly two decades how famous people survive when their birthdays and entire life story is available on wikipedia. I don't understand how that isn't some sort of PII violation. But, life seems to go on for them...
On a slightly different note, I think the nature of your investments may dictate how you structure yourself. Mine are in "quality" areas that attract "quality" tenants. I've had police officers, nurses, lawyers (talk about quality, an attorney was one of my evictees...), etc. Forming a repoire with them I think was beneficial and personally satisfying. They were more satisfied realizing that I wasn't running just a one-off rental property. Many times they thought about my concerns and even put them ahead of their own. On the flip side, if you are in a "rougher" neighborhood where you have to keep responding that you will ask "Mr. Big" that question, well then maybe you need to have a more opaque structure.
Similarly, people have actually told me that they looked me up and saw that I had a number of properties / recordings (not sure if some actually sifted through the public records results). Bottom line, that was good. The "spectre" of lack of information usually gives people pause...
Hope that helps give you some perspective. Good luck.