I have got a very very similar problem to this and I am looking for a solution, too. Here is what I do/did:
1.) I open itunes and restore the ipod
2.) I sync the ipod in itunes in order to get my poker game installed on it
3.) I add some mediafiles to the itunes library in order to complete the installation of a program called i-Workout (http://www.helmesinnovations.com/iWorkout/
) - This adds 178 "songs" to my ipod
4.) I close itunes, disconnect ipod and everything looks fine
5.) Then open Mediamonkey and try to sync my whole collection (about 8000 songs)
6.) At some stage it just freezes. At first I thought that the freeze was happening randomly (it is not even a real freeze it is just that the synchronisation process just does not progress at all, even when waiting for mor than half an hour. The program itself is still responding, except for closing it down). The only way I can close Mediamonkey is to terminate it via Task Manager.
Then I noticed that it always stops at the same album, in fact at the same song. My first suspicion was that there is something wrong with the file, but then again, I used to synchronise this album all the time and it was just fine.
7.) in order to proove that this album is causing the problem, I have deselected all other music from my library (Autosync Options). I am only trying to sync this album now. When doing so, it fails.
Then, I have done another test:
1.) I have taken the song that Mediamonkey hangs on and copied it to another folder that is located one level up in the folder structure.
2.) Then I changed my synchronise settings so that it would point to this new directory.
3.) Now the song synchronises perfectly.
Don´t ask me why, but I have found the following "workaround" (it is not really a workaround, but better than nothing):
1.) I go to the location of this particular album.
2.) I open itunes and drag all files from this album into itunes
3.) I select all files in itunes, then select "Get Info"
4.) I change the album name to something else, then I click ok
5.) I select "Get Info" again and reverse the name change
6.) I close itunes, but I am not syncing my ipod with itunes (the IPOD is not even connected)!!!!
7.) I connect my ipod.
7.) I sync this album with Mediamonkey now and it is working just fine
I have noticed another thing when following the stops in Process C:
I usually embedd my artwork within the tag of each song. In my windows explorer (I actually use Directory Opus, not windows explorer), when I hover my mouse over the songs, it shows me some of the tags (e.g. artist, song name, bitrate etc.) and also the cover, IF!! the cover is contained in the tag.
In the beginning (e.g. before adding the songs to itunes and changing some of the metadata), even though I have embedded the cover art into the tag, the cover did not show up in windows explorer (Directory Opus) when hovering over the songs.
After I have added the songs in itunes and changed the album title (e.g. after step 5.), suddently, the cover art comes up when hovering over the songs in windows explorer (directory opus).
I cannot make any sense of the above, but I hope that a developer may find a clue or has a hinge in any of my descriptions.
Please make an attempt to find out what is happening here as this is very frustrating. It seems that I am not the only one having this problem, so maybe it would be worth investigating further. I am very happy to help out any way I can in order to find a solution.
My suspicion at this stage would be that I am not supposed to synchronise my music first with itunes and then with mediamonkey, but that does not explain why it only happens with selected files and only when these files are in a certain folder.
cpsubrian: Do you do any of the above things similar to me? Can you try to find out whether it always stops at the same song? Could you try my workaround from above and tell us whether it is working for you, too?
Your help is very much appreciated.
PS: I am using version 188.8.131.520