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The problem is that updating plugins very often breaks stuff.

I've been running a heavily customized WordPress with literally dozens of plugins since 2005 and that has most definitely not been my experience.

One I can remember is that Facebook's official plugin stopped working and we had to switch to some other social integration plugin.

Another one was the embeded media player which just disappeared. That was somehow related to shortcodes.

I've only had that happen twice in a dozen years.