Ever?
If you've got a couple of feet of cable flapping about between the plug and where it's next secured, the port will last a much shorter time than if you use a right angle plug and neatly secure the cable near the mount. Similarly, a bit of salty winter road spray or a drop of sweat getting into the port will cause port death where mostly dry use won't.
It is a known failure point, at least one person on this forum has reported such a failure in one thread (which I can't find right now annoyingly).
On my bike I have a 90° µUSB cable, that is routed up through the hydration port outlet of my framebag, and then through the rest of the cockpit crap, up onto the stem, on smooth tarmac there is minimal flapping to vibrate onto the wahoo. However I wouldn't want to leave it there unnecessarily, nor would I want to ride pavé with it in place (not that I ever want to ride pavé by choice if I can ever avoid it).
As detailed up thread, leaving it plugged in, esp without a cache battery between the dynamo and the device is not going to do the device any good. Races like the TCR/TABR/IPWR are unique, the duty cycle of equipment used is just not seen by most cyclists' kit. I've had people in bike shops tell me that the 6hr battery life of a head unit would be plenty long enough for any ride I do. My reply was "I did a 19 hour bike ride on Saturday". The look of horror was worth it. This gets even more fun if you look at events like the iditarod. The grease used by most component manufacturers has a gelling point at about -20°C (Hope use a grease rated to -50°C). When I spoke to shimano about this, their reply was "Why would anyone cycle in that cold?". When I spoke to SON about the temp rating of their hubs, they said the grease they use is rated to -20°C, and there was no scope for a custom unit as they are too over worked. If you look at the rated use temp of devices like the wahoo, it lists "Operating Temperature: -4°F to 122°F / -20°C to 50°C" thing is the actual life of a LiPo battery at temps below 0°C is pretty poor, their performance drops significantly as the temp goes down, what is more you can't charge the internal cells below 0°C, and even at 0°C, the charging rate is pretty damn poor. Obviously this is way beyond the scope of TCR/TABR/IPWR/PBP, but it shows some of the design limitations that are out there in the kit that we use and how the push the envelope of what the kit was designed to do. That said, cycling in NSW in January, in full sunlight the 50°C upper limit may be reached... tho at those temps chances are the squishy bit between saddle and handlebars may be more of a problem...
I had one bike shop guy try to sell me some really good expensive lube, and said I should apply it every 100km. I said fuck that I'm not doing 3 chain lube applications on a single day, that's way too much faff, again look of horror (I should stop playing with the bike shop staff of Amsterdam bike shops really...).
What we do as both Randonneurs and ultraracers is pushing the envelope of what kit is designed to do, it's worth remembering that when choosing out kit.
I'm sure it could happen. All I can say is that it hasn't happened to my GPS, although I have done it regularly for almost a decade, which has included riding on some pretty rough roads. And while I haven't gone out of my way to enquire, no-one has mentioned to me that it happened to theirs.
The plural of anecdote is data...
J