I've been using usb-c for a few years on all my critical devices (phone, computer , tablet, raspi) and in all possible situations (car, desk, night stand, power bank) and never had an issue with the connector.
I'm sure it happens to some people but it can't be a big issue or I (as the "IT-guy") would have heard about it.
Currently my phone charges mostly with the second notebook charger I got from work or one of those cheapish Anker PD bricks.
Anegdotal evidence, but all my USB-C phones (three of them) so far have had the connector fail after 2-3 years of use, and it's not due to lint and dust in the port. Cable doesn't click into the port and falls out on its own.
I think we're all "IT guy" on HN. You are thinking with a survivor's bias. I use to have this problem with android all the time especially when I traveled
I'm sure it happens to some people but it can't be a big issue or I (as the "IT-guy") would have heard about it.
Currently my phone charges mostly with the second notebook charger I got from work or one of those cheapish Anker PD bricks.