Now I have a craving for Surf Taco!
Oh yea, nice tools too, I would of guessed your tools were your fathers and his yours.
I'm liking the easy button too.
Yea, That mystery tool is called a 'can wrench'. Used mainly by the phone company to work on the box on the side of houses. One side is 3/8'ths, can't remember what the other is.
You should have to retract the collar when taking the bit out of the chuck.
The only time that I have seen them come out when in use is if you were trying to retract the retaining collar while inserting the bit. They should just snap in.