Hi GI,
When I was in Oz for a year, I got
crewing jobs by just plain walking the docks and
talking to people. I did the
Sydney to Gold Coast
offshore racing, Club
racing in
Sydney Harbour, a couple of sea trials out to Lord Howe Island on big cats, racing on and then
delivery from Adelaide via backstairs
passage down to Melbourne on the original
Wild Thing - all by just plain ol' talking to people.
Racing and doing the big regattas would also be an opportunity to demonstrate he knows how to sail and what to do on a boat, as well as connect with sailing people who know other sailing people who are looking for crew.
I was like a jumping bean - the next thing always seemed to show up by the time the previous thing finished. Word of mouth is a powerful thing in the sailing community! A LOT more useful than the find-a-crew website BS. In all my years of full-time sailing, I think I can say I
NEVER got a crew position from a website - and I was signed up on all of them.
Australians are incredibly generous and welcoming people! As long as I demonstrated I was tough enough to
pitch in onboard, another position always materialized. He's lucky that he lives in Oz and can always go home for a bit in between
boats. Tell him to also get his YHA card (Youth Hostelling Card).

So if he finishes up a
delivery in
Peru, say, he can just drop his dufflebag at the local hostel for $8/day while he walks the docks to find his next boat.
Of course, I wanted to actually SEE Oz while I was there (plus I was building sea miles for my YM), so I didn't take anything that was leaving
Australia and going elsewhere.... If he does take
offshore stuff going elsewhere, tell him to try and take positions that would land him somewhere at dates/times where the next jobs are there for the picking. For example, participating or arriving for
Antigua Racing Week at the end of April means you can find a ride back across the Atlantic to get a boat job in the
Med for the Summer, at least, if not for longer.
You're right about not
buying a boat or encouraging him to buy a boat. Tell him to get on other people's boats where
they are dealing with the costs - just coach him to be as helpful as he can to sail the boat well. If he's a good kid like you say, he'll get jobs (more unpaid than paid - with the exception of passages - which should have a day rate + plane ticket - but even on the "unpaid" they'll feed you and you
live aboard for free while she's sailing). If they want him to pay anything, tell him don't bother. Waste of time.
Another thought: PM DaleTournier? I know he's back in Oz, but is a
liveaboard... maybe Dale will be back out there soon and looking for crew...?
You're a good man, GILow!

Warmly,
LittleWing77
P.S. Tell him to get an RYA YM Logbook and document all his sea miles (starting with what he can remember of his passages on his family's boat). From then, tell him to document *everything*. That way, he'll have something to show a potential owner as he goes along (plus, you never know, maybe he'll want to do the RYA tests eventually, and the sea miles will have already been accumulated...)