:Destroy from the Client on something that is inside LocalPlayer.Character will not fire .Destroying on the Server

Yeah. This seems like the direct result of the lack of documentation [and making a new policy] for the against-the-FE-grain of having client destructive control of the Character.
Over the years many have posted on the subject and many improvement ideas have been shared as well.
The fact that this has been “swept under the rug” I bet is the reason it was “forgotten” about.

The article on the fixed Destroy() replication (and new Destroying Event) talks about how it is
Server-to-Client, and only mentions in passing the security implications of it going the other direction.

Given this, it appears that the special-case of the local character may have been completely overlooked.

And given this post, it’s not unreasonable at all to assume that this should work Client-to-Server: