5 years is not enough to be experiencing this. The pain is very real and consumes a tremendous amount of effort. I've started writing tools just to create inventories of which packages with which versions I'm using where in order to try to automate the upgrading of virtual environments as much as possible. It's a horrible experience.

The biggest boulder I currently see rolling towards me is the MongoDB driver since I need to upgrade the databases and the drivers can't cope with the latest version.