How I handle updates:

• Create a sandbox for all of my stuff (virtual machine, container, etc)
• Install everything, run all of the tests
• On failures, ask a) whether I actually use that functionality b) whether I agree with the failure -- it might be some garbage test that is checking for POD completeness

I install a lot of modules but only really need a certain number of them. I know which ones are which by adding Test::More and use_ok() calls inside of all my projects for the important ones.