There are two principles that are colliding here:
Therefore it falls out logically that the php user should not be owner of most files, but the deployment user will need to be to be able to write them. However, the php user does create files in media, so they will end up as the owner, and the deployment user may not have access to them.
So you can see why a check on system:upgrade to make sure that media is writable is restrictive and breaks the above need that is only a logical extension of sensible security policies.
@maderlock, thank you for your report.
This seems to be correct Magento behavior. Please refer to the Community Forums or the Magento Stack Exchange site for advice or general discussion about this.
Otherwise you may submit Pull Request with the suggested changes.
Ah, it's "correct Magento behaviour". That would explain the problems I'm having.