The long awaited solution! All I had to do was sit down and "think" for about 5 minutes and it dawned on me. Why not just carefully master a playlist to pull the cover art from the Images portion of Media Center? After working through the entire process, I am now ready to present a complete, easy to understand guide to allow users who utilize the Folder.jpg method of storing cover art to copy the files to their portable player, assuming it supports cover art or images. Remember that the user specific data, such as [Artist]/[Album], may be modified on a user basis and still may work. I will write it from my perspective using my settings.
1. First, verify that your cover art is neatly stored in your album folders, ideally with a common name such as Folder.jpg.
2. I am assuming all cover art will be added to the Images portion of Media Center so now users should open Images.
3. Search for your unique term describing only cover art and nothing more, "Folder." More terms may be necessary to individually select only cover art, such as adding more words to describe the hard drive location, such as the word "Music" for your music folder. The key is to select only cover art in the search.
4. Select all the items and right click, Library Tools, Fill Properties From Filename, check Directories and type your system in, IE: [Artist]\[Album].
5. Create a new Smartlist, type a name, click Advanced, and type in the following criteria--modifying it to your taste:
[Media Type]=[Audio] ([Rating]=>=3 or [Number Plays]=>5) or ([Media Type]=[Image] [Name]=Folder) ~dup=[Album] ~sort=[Rating]-d,[Number Plays]-d -[Genre]=[Children],[Christmas],[Classical],[Comedy],[Halloween],[Meditation],[Nature],[Poetry]
6. This will pull music files rated 3 or more stars and songs you've played a lot on while adding the folder files and sorting in a good fashion. I personally add a genre remover (-[genre]=) to remove certain genres, such as Christmas, until I want to later add some seasonal music.
7. One limitation is that the jpg files will be copied at the very end of the sync.
8. Now, to setup your player, I recommend starting from scratch and clearing your device off (if you can). Plug in your device and name it if asked. Next, go to the Handheld Options (Tools > Options > Handheld). Select your player and configure its conversion settings to your liking.
9. Under Files & Paths, I setup Audio as "Media\[Album]" and Images is the exact same. Remember to add jpg to the list of supported file formats.
10. Now, as an initial test run, it is advised to change the playlist to items played more than 10 times or more to condense the playlist to under 50 items so you can make sure everything is working correctly.
11. Sync!
12. While mine is syncing...oo! I just noticed that it copies the jpg files between copying music. I realized I forgot to push enter after typing the images location in because it was using an Images folder--so I had to stop, format my device, and start over. It's going well right now and estimating 8 minutes for 40 files (about 40% jpg's). I want to test it with a small number of songs first.
The procedure just finished and I tested my device. The cover art shows very nicely and everything seems to be working. I will now fix my playlist to include all my music and let it sync--it will take a few hours.
IMPORTANT: I still need a way to automatically scale down images. Can Media Center automatically convert jpg files like it does audio files? I think they should add a Conversion setting for images for sure and video would be neat, too!