Huh, maybe I'm an outlier. Maybe it's the way you remove your connectors? Some people tend to wiggle them side-to-side, I touch the chassis with my thumb and index finger around the USB, and kind of roll my fingers so they put pressure against the chassis. That leads to the removing force vector pointing strictly straight out of the connector, and I've never had a problem with any port.
Past me was definitely careless. Current me—doubtful, or at least I’d like to think I’d have learned to be nicer to ports…
> I touch the chassis with my thumb and index finger around the USB, and kind of roll my fingers so they put pressure against the chassis
This doesn’t work when you have two ports in close proximity and one of them is occupied. In that scenario I’d have to either lift the laptop in order to squeeze the connector from top & bottom while removing (this option requires not being exhausted or lazy) or pull on a cable a bit further away from the connector (though I do it gently nowadays, pushing with another finger against the chassis for at least some balance).