How can i add custom art to playlist cover on iPad/iPhone/iPod?

I make a lot of custom playlists, with songs from multiple albums and sometimes multiple artists in one playlist.
Most are created on my Macbook Pro OS 10.6.8 (iTunes 10.6.1) and manually copied over to the devices- i don't automatically synch because my music libary is too big and complex. IE, iTunes is set to Manually Manage Music for these devices.
On my i-devices (primarily iPad 2 and iPhone 4), the playlists show up without art work for the playlist, just a generic picture of a musical note, even tho on the source Macbook the songs have cover art.  I find this actually dangerous for use in my car, because it forces me to read the playlist titles. Just glancing at pictures would be much safer, quicker, and easier. But i can't find a way to make all the playlists show cover art.
Playlists i create on the devices themselves DO show a tiled image of all the album covers for the art work.... which is fine. but i can't figure out a way to get playlists that are copied over from my Macbook to show art... and that's the main source of my playlists.
help?
i have too many devices -there's also an older iPod Touch i use in addition to the iPad and iPhone- and too many playlists to create each playlist on each device from scratch so that it shows artwork.
Anyone have suggestions?
(btw, if solution involves upgrading to Lion, i can't; i have software i have to use that doesn't work in Lion).

ps iPad 2 is iOS 5.1

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