The rage comes in when you're already working at 95% capacity, and something simple turns into the mother of all clusterfuck-abortions. For example: You "renew" a Verisign class3 cert, only to find out that the "renewed" cert is in fact an entirely "new" cert because Verisign changed out its intermediate CA. So a drop in file replacement becomes:
Adding the new intermediate and hash symlink to the apache truststore
Adding a FileChain directive to all affected vhosts
Notifying all of your customers that they need to update their truststores in the next 30 days if they wish to continue doing business with you
Realizing that you're going to have to repeat this maintenance for all 400 Verisign certs for the next year (because business partners require yearly renewals)
Having to go through your companies bullshit change-management process, rather than using the rubber stamp renewal template that you spent 2 days creating.
And worst of all, trying to explain all of this to your manager, who has no understanding of the concepts "encryption" and "trust".
5-10 minutes (renew, propagate file, roll apache servers, update asset management) becomes a Full time job for one year.
The majority of which could have been avoided if they had followed your advice "7 years ago" and shelled out for a wildcard cert.