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I'm not quite sure how deep to go here. I have been focusing on reporting errors from 2.0=>2.1 upgrades thus far via CLI. 1.x=>2.1 produces many, many more errors & gaps in functionality.
Browser upgrades are far more robust than CLI at the moment... Especially the further back you go.
Description
Two issues specific to upgrading via the CLI:
Steps to reproduce
Environment (complete as necessary)
Additional information/references
Errors from trying to upload an avatar:
The problem is the folder & url weren't setup by the upgrader:
$upgradeData is still in Settings.php:
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