I'd like to work on this. Looking at the current codebase, here's what I can confirm:

ostype: evaluated server-side — checked against ServerInfo().OSType (the connected daemon's OS) in cmd/docker/docker.go (hideFlagIf/hideSubcommandIf with notOSType, and isOSTypeSupported). Used both as a command annotation (e.g. checkpoint/cmd.go) and a flag annotation (e.g. container/opts.go).
experimentalCLI: evaluated client-side — isExperimental() in cli/cobra.go checks it purely from the static cmd.Annotations map (and parent commands), with no dependency on the connected daemon at all. This is a build/binary-time flag, not a runtime daemon check.
I could not find a plain "experimental" (non-CLI) annotation anywhere in the current cli/ tree — only experimentalCLI. Was this referring to something that's since been removed/renamed, or a different mechanism (e.g. daemon-reported ExperimentalBuild) that isn't implemented as a command annotation?

Given that, the smallest useful fix I can see is adding a short doc comment (e.g. in cli/cobra.go near isExperimental, and near the ostype/swarm annotation constants if we introduce them) explaining what each annotation checks and when it's evaluated (client build-time vs. server runtime), rather than a behavior change. Does that match what you had in mind, or were you looking for something more (e.g. a docs/ page cataloguing all annotations, or introducing typed constants for annotation keys instead of magic strings)? Want to confirm scope before opening a PR.

Clarify command annotations for server or client side #1363

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