I have moved to PC using Cubase.
All my projects on Mac are in Aiff audio format.
When I batch convert the files to waw and load the session, Cubase is asking me to manually link each corresponding file from the pool.
Is there a simpler way of loading the session without clicking around so many times?
I wouldnt think so my man, as even though the file names are the same,the extension is different, so cubase assumes they are in fact different files (which they are) …Cubase would assign them automatically of you had just moved the files from a different folder. and the filename & type are intact… but it cant automatically assign files which in effect, are completely different from the orginal files in the project…
How does Cubase know that the files (which are completely different) are indeed the correct files you want to use in replacement…sorry but no ESP in Cubase, or any other daw for that matter. 
Cubase can only batch process missing files if the file name & type are the same.
I know what your getting at,and it would be neat for users, who migrate files from Mac- Pc…but at this moment I cant think of any automatic way this can be done,but maybe someone else will chime in…
Have you just tried using the aiff files directly?
I am presuming he has done the converting, and binned the aiffs (or they are still on the mac…but if he hasnt then of course there shouldnt be a problem…as split said just move the aiffs to the pc. 