I am re-reading (third time) Anne R Dick's memoir The Search for Philip K Dick - which contains the information that his favoured Monopoly token was the Old Boot - and a critic commenting on the book later suggested that this was significant, in terms of PKD's self-image.
Maybe...
My own favoured token was the Flat Iron; and the reason I gave myself for this choice was the way it could slide smoothly over the board.
The most popular token among family and friends (about which fights would occur) was the Little Dog; which seems an obvious one, because it was cute.
The other die-cast tokens in my game were the Top Hat, Battleship and Racing Car.
In retrospect, it is surprising that I did not favour the car or the ship - so maybe there is some occult significance in the iron - but I am not sure what.
I don't enjoy ironing, and never have; although doing it is indeed one of my current family-household chores.
(Maybe the childhood choice was some kind of unpleasant self-fulfilling prophecy?...)
So, what was Your favourite Monopoly token as a child - and can you infer whether it represented anything about your character?