Is there a way to add a number to the items in a playlist?

Question

Is it possible to number the items in a playlist?  For example, I have books in order and I want to add numbers so I know which one to listen to next.

Answer 1

There is some variation in the way that different models of iPods handle listing of audiobooks - specifically those broken into multiple parts (files).  I have one old Nano (2nd gen) and a current model (7th gen) - the latter (correctly) lists complete audio books in the Audiobooks menu, each book then listed as one or more parts (typically further subdivided into chapters).  The older one just has a list of parts (ordered by Name or, if set, Sort Name).
The method that I use to get as consistent listings is possible is to set both Sort Album and Sort Name metadata elements as shown in this example:
Notes:
This is an anomaly since the actual book title starts with 'A' which iTunes will automatically strip and set the result as the sort name.  Explicitly setting the Sort Name to the full title overrides this.
This is a three-part audiobook (i.e., three files)
This is how I handle series - so these three files (one audiobook) are the 3rd volume of the "Sherlock Holmes" series.  Using 01, 02, 03 rather than 1, 2, 3 allows for series that run to more than 10 titles.
Since the Name values start with "The" iTunes strips this off to automatically create a Sort Name.
Another example of books in a series, where each audiobook is made up of two or more parts
This is the standard I use for (almost) all multi-part books - set the Name value to <title> - Part <part no.> ... note that as in example (4) iTunes automatically strips "The" to generate the Sort Name
This is an exemption to the rule illustrated in example (6) - its a 12 novel sequence, each with an individual title (Name field), published as four audiobooks each split into three parts.  The Sort Album values ensure that the audiobooks themselves are ordered correctly; the Sort Name values put the individual novels in the right order.
I'll freely admit that this isn't simple, and that it took me several rounds of trial-and-error to finalize a scheme that works for me.  Obviously you could achieve very similar results by prefixing Name and Album values with serial numbers - I prefer not to do this for largely cosmetic reasons - I like titles to be "proper" titles, not numbered items.  Turingtest2 has a script on his site that takes a slightly different approach (though fully automated) - I tried this but found some issues with portability across the two iPods that I routinely use for audiobook listening.