In at least one of the cases, this was because of stuff (some sort of gunk) getting into the port. Before anyone says that wasn't a problem with the port itself, having a physical port allows problems like that to happen. Problems of that sort don't exist with wireless technologies.
Heh I know it's technically possible if you jam a candy bar into it, or spill coke on your phone, etc. It's much less pervasive than Bluetooth cutting in and out because you put your hand over the antenna and similar problems, though.
I got what you meant, I just meant that if you had a 3.5 mm jack, you wouldn't have these problems, it would just work. We've replaced a very simple, cheap solution that works very well and has very high fidelity with an unreliable, expensive, complicated one that has worse sound quality when it works. Your problem could very easily be avoided with very old tech.