Anecdotally, I don’t tend to run into connection issues with wireless keyboards—I do with wireless mice, however.
Luckily, in USB-C, the springy bit is in the cable, so that's where the wear and tear is. If it stops working, the cable is generally easy to replace.
> 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).
The most flaky removable thing I've encountered is microSD cards, and I don't know if it's the card or the reader, but they tend to only work half the time. I even check them for authenticity of space, so I don't know why they're so flaky.
Is it easy to source replacement I/O boards for Framework?
But on the original topic, it appears that modern wireless keyboards fare well enough as far as connection and latency[0] to qualify for gaming, so I wonder if your impression about connection reliability could be a bit outdated?
[0] https://www.rtings.com/keyboard/reviews/logitech/g715#test_6...