Where "Couldn't Organise a Chook Raffle" Comes From
A "chook raffle" is a real and still very common Australian tradition — a low-stakes raffle, usually run in a pub or club, where the prize is a fresh chicken (or these days often a meat tray). It's about as simple and forgiving a thing to organise as exists: sell some tickets, pull a name, hand over the chook.
Which is exactly the joke — if someone "couldn't organise a chook raffle," they've failed at a task so basic it's hard to get wrong, so there's no hope for them with anything more complicated.
Source:
"Don't put him in charge of the schedule - he couldn't organise a chook raffle."
How Aussies Actually Use It
It's used to describe someone (or a team, or a government) making a mess of something that should be straightforward.
It's usually said with exasperated humour rather than genuine anger.
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