I booked in March 2001 for travel in July 2001. I was able to get NY --> Tokyo (Delta), Tokyo --> Seoul (Korean Air) and Seoul --> Bombay (Korean air) without a problem. I travelled to Delhi on my own and bought tickets on Singapore Airlines from Delhi to Austrailia and Singapore (it wasn't too expensive from there). As I said before, getting Sydney through the RTW award wasn't possible because I would be going North - South.
When I got back to Delhi, I continued my RTW trip and went from Delhi --> Paris (AF). I wanted to go to Cairo but that was illegal routing as I would be going backwards from Paris --> Cairo.
The only problem I had was from my Paris --> NY segment. A lot of poeple from the US are vacationing in Europe and award seats are a problem But I eventually did get it for the date I required.
If you are going with the 240K award, I believe you are not bound by capacity restrictions, right? So you would not have problems with dates, only routes. Still if there is a cheaper award available with capacity controls, you should atleast take a look to see if you can get the dates your nephew wants - you'll be surprised that there would be award seats available when you least expect them.