Hey,
I got back from a RTW a few weeks ago - one of the stops was Cuba. We ended up scoring a *A ticket in J and we used Air Canada for our Cuba leg. I looked at all of our options and at the end of the day, AC via Vancouver/Toronto was the best option when looking at inflight service, convenience and better airports to connect through as some South American airports are shockers. Connect through Canada and you avoid the whole US embargo hoohah and any related issues. As someone has mentioned, AC has a almost seamless connection from SYD right through to Toronto. Then its a 3 hour flight and your in Cuba!
LAN would be interesting but hmm... don't think I would brave a transpacific with them.
On another note, Cuba was exotic indeed. Can't say it was my favourite destination, but it certainly opens your eyes. These people are poor as - makes you feel happy for what we have here in Oz.