I have kind of a long complicated story that I’m guessing nobody really wants to hear so I’ll cut to the chase.

Your proposed strategy may make litigation after a claim arises more complicated and costly for you to defend.  

It's not that complicated.   

Its not real complicated, its purely a math question.

However, due to it being:1) In the state of California2) A shared home, rather than an outright external property being rented...the default insurance company on offer advised that many carriers are pulling out of CA and that I should go to a local insurance agency.My current insurance for home policy does not offer a "home-sharing endorsement" but only a separate renter's insurance, which would complicate things, since it's for traveling professionals, and they're not going to be booking for 12 straight months.

In most cases, neither is warranted.Warning: I am not an attorney, and this can be a complicated topic.

Complicated rooflines, modern details that require a bunch of steel framing, excessively large great rooms, spa-like bathrooms, etc would push you into the $1,000-2,000 range.  

You raise a lot of good questions.Regarding USD fiat, it gets a little complicated, but most dollar creation is actually done by the banking system via debt. 

In most cases, neither is warranted.Warning: I am not an attorney, and this can be a complicated topic.

Some areas may have restrictions that could complicate things, particularly around who can provide alcohol and to whom.If wine isn't an option, you could consider alternatives that are still local and personal, like a handcrafted bottle of olive oil from a local farm or even a basket of locally sourced snacks.