BUG: Master Properties Time Remap
I've noticed this issue, and have finally figured out the cause. Now I hope you can fix it.
If you use time remap on a layer that has Master Properties that you wish to keyframe, the keyframes may behave erratically. They won't do anything if you extend the layer past it's original length. In fact, they only work during the original un-remapped time of the layer.
Further—and this is the part that led to this discovery—the timing of those keys is tied to the original layer, and then retimed. So for example, if your original layer is retimed, so that everything happens ten frames earlier, whatever master properties you have keyframed will also happen ten frames earlier than your keys.
If you happen to put keys in an area that is sped up, your key values will also not seemingly match up since they're being applied, then remapped. It's confusing to explain, but hopefully it makes some sense.
I can't attach a project at the moment to demonstrate because I can't share this file. But if you set up a comp with master properties, and bring it into a new comp and time remap it and try to keyframe the master properties, you'll see what I mean. It's very erratic, especially when you're surprised by it.

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Joe Clay commented
I figured out how to explain this more easily. Master Property keys on a layer apply inside the comp first THEN are remapped in the main comp. So in the main comp, where you can see all of those keys, it makes absolutely no sense because Master Property keys can apply to a completely different timeline.
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Joe Clay commented
I'm on 15.1.2 on Mac OS X, both Sierra and High Sierra. On a MBP and a Hackintosh so it's either OS or all AE versions. Due to how it exhibits, I'd say it's probably a bug in all versions.