Playlists would work if the headphones can use them. But if they only read the file name and sort in that sequence, then you must rename the files so that they sort in the order you want.
I thought of using the
Sync Handheld functionality, but that only rename directories and not file names when it is used to sync to a device, such as a memory card.
That leaves you with using the
Rename, Move, & Copy Files function to mass rename the files so that they sort as you wish, just as StFeder suggested.
Would not it be easiest to change the order in the filename? So that the album title is first and the track number second? Then look like this:
First Album - 01 - First Title
First Album - 02 - Second Title
Second Album - 01 - First Title
Second Album - 02 - Second Title
So, assuming that the headphones only sort by file name, that it can't read tags at all, and that audio books are the most difficult case, this is what I would do;
Add a field to the Library, perhaps called [PlayOrder]. Make it an Integer. "Options > Library & Folders > Manage Library Fields...".
Insert the
empty memory card into a reader connected to your PC so that it has a visible drive letter. If not empty, delete the contents, as you are effectively doing a refresh of the books on the card, not a synchronisation of files.
Create a playlist of the files you want to put onto the memory card. Sort it the way you want it sorted, so probably by [Album]-[Track #], where [Album] is the audiobook name, and [Track #] is the chapter number.
Add the [PlayOrder] tag as a column into the Playlist view you are using so that you can populate the tag.
Select all files in the Playlist, and then rename the [PlayOrder] tag to "=Counter()" without the quotes. The [PlayOrder] tag will be populated with numbers 1 to x, where x is the number of files.
Press F6, or right-click and select "Library Tools > Rename, Move, & Copy Files".
In the Rename, Move, & Copy Files dialogue set the top drop-down list to "
Copy".
Make sure it is just "Copy" and not set to update the Library.Tick the Directories box and set the Base Path to the drive letter of the memory card.
Clear the Directory rule.
Tick the Filename box and set the rule to "[PlayOrder] - [Album] - [Track #] - [Name]", or something similar, as long as the first tag is [PlayOrder]. The rest of the filename just makes the file name human readable.
You will be able to see the proposed file names and their sequence on the right of the dialogue.
Click OK and wait for the copy to finish.
You will now have a set of play order sequenced files on your memory card, ready to insert into the headphones.
I tested the above. It works.
Of course, each time you start to play something in the headphones it is going to start from the beginning I assume. Unless it remembers where it was up to, your kids are going to have to jump forward through the files to where they were up to. Not ideal, but the above method sorts the files the way you want. It would be pretty quick and easy to do as well. You could easily update the Playlist and re-copy so that unread books are moved to the beginning of the order, but read books are still on the memory card, just later.
Really the above is just to give you an idea of what you could do in MC to get around the shortcomings of the headphones. You will probably want to adjust the process based on information I don't have.