Multiple properties with multiple LLC's...looking for insight

[Brandon Jones]

Hey everyone — looking for some insight from hosts who own multiple STR properties and have set up some kind of asset protection or entity structure around them.

For context, I currently own and self manage 9 short-term rentals.  Last month, I had a big scare: a tree fell at one of my properties and almost hit a guest — a true near miss. Thankfully everyone is fine, but it really opened my eyes to how much liability exposure I have.  

Because of that, I’m working with my attorney/CPA on a structure where:

I have one operating/management LLC for all day-to-day operations (bookings, payouts, cleaners, supplies, vendors, etc.)

And then five property-holding LLCs, each owning 1–2 properties and holding only the real estate/equity (no daily operations run through them)

I like the liability separation, but I’m still trying to fully understand how people handle the day-to-day workflow with this setup.

For those of you who own multiple properties and do something similar:

How do your daily operations work?

How is your insurance structured?

What has been the biggest challenge with this structure?

What has been the biggest benefit?

Anything you wish you had known before you set up multiple LLCs?

Not looking for legal advice — just hoping to learn from owners who’ve actually been through this and can speak to real-world operations and insurance.

Thanks in advance to anyone willing to share!