If it is an outside liability claim (like someone suing you because your son killed someone with your car in a crash), if the LLC is set up in a proper jurisdiction with charging order as sole remedy (or your LLC is owned by a holding LLC in such jurisdiction), then the plaintiff would not be able to reach into the LLC asset.You can combine both by having the property owned by a land trust where the beneficial owner is an LLC.Using asset protection structures can be very efficient in protecting your assets from catastrophic lawsuit by limiting the risk to only part of it.

The thing I'm getting at here is there will always be unanticipated catastrophe's that could make your investment turn out poorly. 

I've also made the acquaintance of quite a few interesting people.Fortunately, while this incident has been a significant setback, it nowhere approaches the catastrophe with which many of our fellows are faced because of the wide spread consequences of the pandemic. 

Not to mention the catastrophic lawsuit you could be facing.Please BP folks - do not give advice outside of your expertise. 

Catastrophic weather events, fire, etc. can also happen.

You can never insure enough in the event a catastrophic event happens at the property.  

Do you have some sort of strategy to be so aggressive that also prevents some sort of catastrophe down the road?

Will the real estate market suffer a catastrophic meltdown as well?

Both areas have a strong history and other than some catastrophic event there is nothing in the foreseeable future that would change that.You also seem to be wary of Vegas long term. 

I don't know if this is the case in HI or with your policy, but I have seem some insurance policies in my day that have a "waiting period" for catastrophic coverage.