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I see that no one replied to this post last week and I am guessing you may have done your upgrade at this point. Have you encountered any issues during the upgrade and did the extract upgrades meet your expectations?
I updated our server that host the visualizations for the Tableau Community and found that the upgrade took about the same time as previous upgrades I have done but we only have a few extracts on this server so I did not anticipate any sort of issue. On the positive side, the use of the date filter for the Ideas and Crow's Nest visualizations is significantly faster with the Hyper extracts than the previous .tde based extracts.
I hope that helps a bit but I'd love to hear/share customer experiences.
Jonathan - i also noticed you were asking about the time impacts for the upgrade. The extracts are not automatically upgraded as part of the upgrade so the time difference related to this should not be considered. Upgrading of each extract on server is done as they are refreshed/rebuilt. See - About Extract Upgrades from .tde to .hyper for some detailed information on that. Some server administrators are kicking off extracts after an upgrade of each of the data sources to force the change to hyper but there is no automated piece as part of the upgrade.
I hope that helps.