It seems to me that the problem is on boot, I have found that: 
- If I boot without a device then it doesn't work, it happened to me with a USB 
to serial (not creating /dev/ttyUSB0 and also with pendrives /dev/sdx
- If I boot with the device, then I can plug / unplug without issues, even new 
devices of the same type (different pendrives)

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https://bugs.launchpad.net/bugs/1589997

Title:
  The device on /dev/sdx is not created when inserting new devices

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