Hi Ed thanks for the great questions. As you've identified this a very complicated topic.
• Is it intended to work this way? : If this questions is asking whether we are aware of the current behavior, then yes. If the question is whether this is the long term "right solution", then no. We do want to support updating the user and group entities on EACH login, just have not yet implemented it. It is on our radar, but has not yet been formally prioritized. That being said, it should be medium effort to do, and we'd gladly accept a contribution here.
• Wildcard Matching in Policies: To be honest, we are being very careful about releasing wildcard matching; we aren't confident that users should be exposed to the internal details of how URNs / primary keys are constructed. That being said, once we have captured "containers" (databases, schemas, collection of assets) on DataHub, we do intend to support predicates based on those. Perhaps you can detail the use case you are trying to achieve?
• View Based Policies: Tentative timeline is first quarter of next year, but we'd really like Community participation to help move this item along more quickly. What types of metadata are you hoping to restrict?
• Proactive Privilege Indicators: We are aware this is a bad experience that can cause a lot of pain. Implementing this is non trivial amount of effort, however. We recommend that Administrators communicate user's privileges to their users until this is implemented. However, I'd also consider this to be "Phase 2 Policies" work that should be included in the Q1 next year deliverables. How urgent is this for you folks? I'm assuming lower that the other asks you've raised?