Well, I haven't restored mine recently so I can't say for sure it'll work, but the option is there for v11.4:
As for the auto-playlists, I can transfer them to the iPod, but they will only function as a normal playlist. If I view the iPod in itunes, the playlist doesn't display the gear icon. This really only matters for AP's based on track ratings, which can be altered in the iPod.
I'm not sure how MB generates thumbs for viewing ipod files If tracks were transferred to the ipod using itunes, MB displays the thumb as empty. Tracks transferred with MB result in thumbs from random albums from the same artist:
*off topic:
Yeah, I did the battery myself. Ordered a cheap one from ebay and works great. Just make sure to get the right one (I think there's 2 sizes for these Classics and ebay ads can be confusing). Lots of vids on youtube, but I found this to be the best one:
https://www.youtube.com/watch?v=6aQn-HkvtvM