Ensure make dev-env support rolling updates

[aledbf]

What this PR does / why we need it:

Types of changes

• Bug fix (non-breaking change which fixes an issue)
• New feature (non-breaking change which adds functionality)
• Breaking change (fix or feature that would cause existing functionality to change)

Which issue/s this PR fixes

How Has This Been Tested?

Checklist:

• My change requires a change to the documentation.
• I have updated the documentation accordingly.
• I've read the CONTRIBUTION guide
• I have added tests to cover my changes.
• All new and existing tests passed.

[k8s-ci-robot]

[APPROVALNOTIFIER] This PR is APPROVED

This pull-request has been approved by: aledbf

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[k8s-ci-robot]

@aledbf: The following test failed, say /retest to rerun all failed tests:

Test name	Commit	Details	Rerun command
pull-ingress-nginx-e2e-1-16	b751661	link	/test pull-ingress-nginx-e2e-1-16

Full PR test history. Your PR dashboard. Please help us cut down on flakes by linking to an open issue when you hit one in your PR.

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