Clearly an XY problem. You should not be having any data loss over USB so the solution is to find the cause of the data loss and fix it instead of doing some insane soldering project.To answer your original question. It would be extremely difficult and require advanced soldering skills. The resulting connection would be fairly fragile. You could glue the wire to the board to provide some strain relief for the solder connection, but you would still need to be very careful not to yank on the USB cable.
I'm a beginner with arduino!