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When I used another mp3 player, I used to use scripts to automatically rename each file based on creation date, and the player would play them sequentially.
At the time that I went to an iPhone, I happened to have about 16 months of podcasts backlog (about 10 hours of shows a week), so I wanted to use the double speed playing capability to be able to catch up to real time. 16 months of podcasts was also a huge amount of data , so I could only transfer chunks to the iPhone. I started by setting it to never sync any podcasts.
At first, it really sucked, since iTunes, etc can't seem to deal with things based on filename, so I had to do a lot of manual playlist ordering. But as I started using itunes to suck down new podcasts, I could use a smart list and Release Date to order new ones.
To get them onto the device, since I don't sync any podcasts, I take the next chunk of them to fit onto the iPhone, and change their type to Audiobook, which I do sync. (I also routinely manually set all podcasts to Remember playback position and Skip when shuffling).
Doing this lets me use the audiobook's 2x play speed on podcasts, which is why I have caught up to within a couple of weeks over the past year.
I still think iTunes is the devil.
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