It is usually cheaper to insure them individually as you can better match the risk to the best carrier.

Now there may be an argument on the part of the carrier to exclude coverage citing gross negligence.

You could work with a broker who specializes in high-risk properties or look at surplus lines carriers that insure wildfire-prone areas in California.

Also check with an independent agent to find the best carrier and rate for coverage.

I don't think any particular program or carrier is one size fits all though.  

Quote from @James Radford: Quote from @Ryan Carriere: @James Radford personally, I would be careful about this strategy of converting a property from an STR to an LTR right away the following year.

For example on older homes with Trane, Carrier, Rheam AC units I've seen those last for 40 years. 

It’s basically “let’s name everyone and see what sticks.”Right now, the best thing you can do is exactly what you’re already doing:• let your attorney handle communication• wait for your homeowners/umbrella carrier to respond (they may cover defense even if the claim is weak)• don’t admit fault in writingKatie, I really hope this helps you a bit, I sent you a DM on BP... it's one of the reasons I do this, I hope you can assist. 

The payout is based on the cost to repair or rebuild what was damaged, not the total amount listed on the policy.Additionally, to ensure you’re fully covered, carriers require that you carry at least 80% of the property’s replacement cost.

@Matthew Crivelli Obie now works with brokers as well so you can get a quote from Obie and other carriers at the same time.