People worked their asses off to avoid Y2K, everything needed to be tested, patched, and tested again.
Unfortunately we have not been as vigilant about security. We're barely able to handle script kiddies armed with a bot army of webcams. We're completely unprepared for when a nation-state actor declares electronic war.
You're right that as we get more and more automation going on our exposure surface grows dramatically.
Now, when cars/trucks become fully self-driving ... now you have a scary scenario ripe for hackploitation.