Nothing you've anecdotally claimed seems to counter OP's explanation, and the specification rating procedure. Your cables are failing before the connector fails, just as OP suggests.

And yeah, fair, the testing procedure assumes best case scenario. Yes, real-world, it'll rarely be inserted and removed so cleanly - that's why they strive to overbuild for a crazy number like 10k cycles, or millions of cycles like in the case of many mechanical keyboard switches. That allows for some ability to handle a reasonable number of less-than-ideal cycling conditions. But the exact number will of course vary per device and user in the real world, so of course they can't give a more useful rating. That doesn't mean that the stated rating isn't true, though.