I guess there is no way to escape the extra stress to the port. Maybe using this kind of detachable magnetic adapter can help with reducing the strain? They don’t conform with usb specification though, so while it may reduce strain to your port, it may carry another risk like making it easier to accidentally shorting some exposed pins.
Nice, I did not know such a connector existed - that will be useful for completely different and unrelated use cases.
While I had toyed with the idea of a portable, Japanese - made DAC for a while, I switched to Bluetooth headphones years ago. Started out with a cheap Philips headset for $50, later on got the Bose QC 35 II (still my daily driver when outside) and finally worked my way up to the Sony WH-1000XM5.
I did not realize how nice active noise cancelation is. Plus, the frequency reproduction of the XM5 with LDAC enabled is absolutely fine.
On the cons side, you’re walking around with $300 - $400 on your head, which is an absolutely luxury, plus you’ll get headphones that perform equally well in the sound department (minus the excellent ANC and freedom from cables) for a lot less.