There is a possibility of an electrical short within the tablet. Since this is a Surface 2 you are talking about, other 2nd generation tablets have loose volume rockers and other details which may be display "slapped together" construction at the factory and no inspection.
If the flash drive works in other computers 100% of the time but fails on the tablet, I would see about sending the tablet back. This is probably a little more of a problem than just the USB socket.
However, if you put the flash media in different computers and get a disconnect or not recognized by the other computer, that will be the flash drive itself.
Flash media of all types (SD, micro-SD, USB pen drive, etc.) are not totally reliable. They do wear down with age and last only about two years with heavy use. After that, you will notice data loss and time to throw them away.
I am getting to suspect that it is the USB port or the internal circuitry on the main board. That cannot be repaired by anybody. Those are built by a computer. The only thing you can do if you can pin point the error to the tablet itself, your only option is to get a replacement via warranty. Definitely defective.