Have you tried cleaning the port out? My last phone had issues with a wobbly cable and not always connecting when I plugged it in. Turned out a bunch of pocket lint and other debris got packed in there, and once I cleaned it out it worked like new. Had to do that twice in the 6 or so years I owned that phone.
Yeah, go for a good quality one like a Spears or a Cepex. Those hardware store white ones get brittle, lock up, and snap like you saw. I spend the 30-40 on one of the good ones and it stays smooth forever.