This particular filter looks like it had never been changed, so it was way past due. If I remember correctly, a fuel filter should be changed out about every 30k.
Not sure about the other questions - I'm pretty sure that the Orange Ring is supposed to remain affixed to the quick release component, or else there won't be a proper seal. If you can see the green o-rings on the inside and the orange piece is removed, it may be too far gone. At that point, I was unable to get a good seal. Thought about somehow affixing the orange piece back in place, but have decided to get new line instead.