Just found this post. I have the same same issue with my Kenwood. See this post.
http://www.mediamonkey.com/forum/viewtopic.php?f=12&t=67549
Navigating the Ipod from the head unit only works after ejecting the Nano using Itunes. I have not tried anything with playlist yet.

Hi,

thanks for detailed information. However, this is very tough to resolve for us, since we don't have the actual device to test iPod with. Since this isn't documented, normally we test by adding/removing individual parts of the internal iPod DB, which we can't do in this case. :-(

That said, if you want to try something more, you could start by trying to replace Library.itdb in the non-working DB from the working set you sent me. Drop me an e-mail with results, so that we could continue then...

Jiri

This bug is now ticket ID NPF-529950.

When I sync my Ipod Nano 6th Generation with Media Monkey, the Ipod cannot connect to my 2010 Lexus RX450h with Nav system. The Lexus reads the Ipod then pops up: Cannot read from USB device or iPod.

I've debugged this for awhile and found two things:
• After syncing with MM, if I open Itunes with the Ipod connected then close Itunes, then the Lexus plays the Music fine.
• However, one of my synced play lists is missing from the Ipod. (existing bug talked about here http://www.mediamonkey.com/forum/viewtopic.php?f=12&t=67106&p=344004&hilit=playlist#p344004 )

I have followed all of the threads for syncing an Ipod. Itunes and MM are both configured as suggested.

Here is my configuration:
• Windows 7 Ultimate 64-bit SP1
• MM V4.0.6.1501
• Itunes V10.6.3.25

Here are the steps I use to repro the problem:
• Reset the Ipod to factory settings in Itunes
• Configure Itunes per suggestions.
• Close Itunes
• Open MM and configure per suggestions
• Use MM to Sync two playlists containing the same single song (128kbps mp3)
• Eject Ipod
• Observe that the Ipod appears synced via the screen and earbuds
• Observe the failure on the Lexus
• Plug in Ipod
• Open Itunes
• Eject Ipod
• Observe that the Ipod is missing one playlist
• Observe that the Ipod works in the Lexus (except for the missing playlist)