The Proclip and Intelliskin options seem the most promising in light of the way tablets are made now.
The reason I'm asking is the Lightning connector on my iPhone, which is a little like a reversed type-C USB connector, has failed rendering an otherwise perfectly useful phone basically a paperweight for mobile uses. I can still get it to charge at home by hanging the phone from the cord just so, but it's a matter of do not touch until it's recharged so it's a stop gap. It's only a 3 year old phone and it's never been abused and just got used to administer the phone as intended. I have used it mobile maybe half a dozen times so my thinking is just preemptive as I anticipate it being an issue with a tablet (which admittedly is my first of any kind, so I have zero experience to draw from).
I think the theory of using a connection that mates once on the tablet and moves the issue to another that can be easily replaced will be fine. I mean, a tablet should handle a few dozen mates with zero issue and I'm sure there's plenty of other ways a mobile installation will hasten it's demise anyway.