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This sounds like it would be a great use-case for the runtime API <https://github.com/pulumi/pulumi/issues/3901>

You could separate your resources into two stacks, one for the operator and one for the custom resource. After provisioning the operator, you could perform readiness checks from within code before doing the second update.

We're working on design for runtime, so please update the issue with your scenario if you have additional ideas or details to share.

<@U012K5A8ANR> Another thing in the near term might be to consider something like <https://gist.github.com/lukehoban/fd0355ed5b82386bd89c0ffe2a3c916a#file-waitforjob-ts-L20>.  If your CRD already has a defined notion of "done" either in the CRD status, or in some API you can reach based on the provisioned status, you could use a little function like that to wait for readiness, and then have other resources depend on the output of that function.