The whole high level communications infrastructure on the Newton is fairly complex. It takes place mostly in the NewtonScript layer and is therefore built on cooperative multitasking: Instead of using threads and semaphores, callbacks are used. This requires much more careful design...
Anyway, the OBEX transport now works over IrDA. It does not handle error cases gracefully and contains no user feedback. But it is integrated in the Newton's I/O box mechanism so sending and receiving over IrOBEX just looks like any other transport (e.g. email). I can currently send text files to my cell phone or a desktop PC. This includes everything that has a textual representation on the Newton: Notes, Names, RSS feeds, ... Receiving files is not implemented yet but is hopefully not too difficult.
It will get interesting as soon as more routing formats are supported. iCalendar and vCard are one example. Routing formats are independent from the transport and can be used over any transport. The sending part of iCalendar and vCard is next on my todo list.