Even at the Fortune x00 companies I've consulted for, I believe I would have been able to get that approved. Any time you are asking people to manually administer boxes, those people are going to want tooling for that job. Manual deploy takes 8+ hours and sometimes ssh sessions time out or are interrupted? We'd like to install a persistent session management tool.

I'm not sure if you're saying that myopic management won't see a business justification or that there truly is not one.