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Sounds like you've got part 1 figured out...
The most recent data showing up upon refresh is a VERY common request, but unfortunately (and don't ask me why) there's no fast and easy (built-in) method to get the most recent value to display in a filter for discrete (blue pill) dates currently in Tableau. There may be some workarounds, but I haven't found any that were really easy to implement--so I'm forced to refresh manually each time new data is added in scenarios like this.
May want to vote for these related ideas:
(there are others requesting similar things as well)
As a workaround, you can use a continuous (green pill) quick filter and it will automatically add new dates when refreshed. The problem is with discrete date filters. I've attached your example with a continuous filter, but understand that's not what you want.
Thanks, Matthew! It really surprises me that I can't default my quick filters to max 1 date and have it update with a refresh. This is going to be a pain since I have these date drop downs on a significant number of charts in our dashboard. I might be able to convert a few to continous, but not all. Thanks for the tips.
Agreed, this needs to be resolved in a future release! More easily created dynamic dashboards, in general (like Dynamic Parameters, the #1 voted for idea in the Ideas section of the forum) are a great need for all of us users.