You might be better off just exporting the raw tracks to a folder along with a detailed text file on track contents.
If im correct, your sending this to another producer to mix down, so exporting any automation is not really a factor.
Your basically sending him raw tracks of the project that line up/in synch.
I do this quite a bit and created a thread in the techniques section of this forum
http://forum.cakewalk.com/Orginizing-Labeling-Audio-and-Midi-Tracks-m3448904.aspxOn how label everything to send it out. I uploaded a Word template as well.
Stems are groups of tracks IE- Sub mixes, Bus mixes, Drum mixes,exc.
If your producer wants individual tracks and not groups, export the tracks.
Im not sure why OMF is crashing I really cant give you any insight on that to be honest.
But like I said if your producer is going to mix the project for you I wouldn't worry much about OMF.
(I could be wrong but I believe you'll only be missing tempo changes, markers and automation)
In my travels, I have found it is best to make sure everything lines up correctly
(bounce all your clips together to create one whole track VS. 20 clips on track 10).
Place a dummy note at 101:00 on your midi tracks so they also line up from project start, this way everything is totally in synch.
Send him a detailed report of tracks (he will love you for it).
And do as much house cleaning (what I call pre production): Melodyne fixes, Autosnap/synch corrections before you send it. This not only saves your producer from headaches but will also save you a few bucks.