This function works great, but I have a couple of issues:
First: If I try to convert more than one file at a time, Media Center freezes. (Intel Core2 Extreme 2.93 GHz Quad 1067 MHz, board Intel D975BX2, XP SP3) If I set Sync Handheld to convert one file at a time it works okay. BTW, I can use the Analysis function on several files at the same time without any problem, although I generally do it one file at a time (less stress on the CPU).
Second: As I watch the Sync Handheld function working, I see ERROR next to some files, but at the end of the process MC does not provide me with a list of what those errors were. I have taken to doing screenshots during the Sync Handheld run, which is really silly. There must be a better way -- for example MC could show a list of these ERROR files at the end of the Sync Handheld run. BTW I believe that the reason the Sync Handheld function is failing for certain files is file names with unusual characters and/or longer file names, or long paths on my hard drive. I experienced a similar problem with Cover Art: As soon as I shortened the path and/or removed the unusual characters (e.g., ";" or "~"), I had no problem attaching cover art to tracks which would previously hot take it. In general Media Center is able to import, recognize and play certain files which it is then not able to work with in other ways. In some kind of Ideal Universe there would be a file name cleaning function which would help with this.