Just for any future readers, we investigated the update issue with v5.0.0-5.0.2 a little whilst ago and some servers will now allow the update to work with those versions.
The fix, as mentioned here is to update to the latest version of Event Espresso, version 5.0.3+ should fix the updates through the dashboard so once you have manually updated to the latest any future version should update as normal.
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Support forum for Event Espresso 3 and Event Espresso 4.