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I believe the reason your second policy variation with the root principal isn't working is because of the special set of rules that apply to just two types of resource-based policies in AWS, one being these IAM role trust policies (also known as assume role policies) and the other being KMS key policies. The rules are different from those that apply to all other resource-based policies in AWS.
I think the second variation should work, if you additionally grant the corresponding sts:AssumeRole permission in the identity-based policy of the role. You can avoid the self-referencing problem in CFN for the identity-based policy by declaring the policy as an AWS::IAM::ManagedPolicy and attaching it to the role (with the Roles property of AWS::IAM::ManagedPolicy), rather than declaring the role as having the policy attached to it (with the Policies property of AWS::IAM::Role).
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