My subjective impression as a web user since the late 90s is that now things break relatively rarely (I think it's the first time I have any such issue with DDG for instance) but when they do a huge chunk of the web becomes unreachable.

Back when things were more decentralized individual websites and services would have issues much more regularly because the individual software and hardware stacks weren't as robust and fault-tolerant, but then usually the problem would always be limited to a single website/service.