It'll never happen but I'd love to see a new analog audio connector designed with portable audio and extreme durability in mind make a debut. The old 1.44mm connector is nice for its ubiquitous nature, but its internal footprint is large and it's prone to contact issues over time (I'm sure most of us have had a device/headphone pair where the jack had to be rotated into a "sweet spot".

I'm not well versed in the world of port design, but what comes to mind is a little shallow magnetic nub with a couple of contacts on it. Easy to clean, impossible to break by accidental torquing, not deep enough to get stuff stuck in it.

The cool thing is that whatever the new design is, making adapters for 1.44mm to the new thing is dirt cheap since it's still just an analog connection.