This word means that the nature and laws of events are very similar, and it is not necessarily a bad thing. It is only used to describe two or more things with high similarity and roughly the same rules, from which we can find some characteristics to sum up.
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Describing two or more things is very similar, right? So, for example, every year freshmen come to school with enthusiasm. The repetition of this kind of thing year after year is not as high as "history is always strikingly similar", is it? Did he describe it as a language barrier?
It is necessary to answer the recorded events expressed by the word "history" to some extent. History will not record some small things and little people, which is why many people in ancient times tried to stay in history.
As you said, the enrollment of freshmen in the school is almost the same every year, which is the smallest thing. The word "history" is not appropriate to describe it. Freshmen entering school is a very common thing, just like eating and drinking water. Will someone say that eating every day is strikingly similar to history? In addition to "history", the word "history is always strikingly similar" also highlights this point, that is to say, the events described should be sensational and surprising, making people think back to the past through what happened later and sigh that "history is always strikingly similar".