I have exactly the same question. It's always been a nightmare manually updating all my rules as I cross over into a new year and it never seems to get any better.
I would be nice to know what Timestamp means on the rule but also just exactly how to either erase what's in iCloud Drive or to dirty the local changes so they are seen as being more recent and not overwritten.
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I would agree with this. Apple needs to stop making the Desktop look like an iPhone. They've changed something that's been the same for years and I'm still looking in the middle of the screen for my login details but now it's at the bottom with no option move it back to the middle. What has happened to the UI experts that Apple was previously known for?