Not sure what you mean by "maximally useful"
As well there are several formats for burning MP3s ie (iso9660, udf, mixed-mode formats) so again it seems dependant which format you are using now.
I see no reason why technically it wouldn't be possible to have mp3 & mp4 capability on a player - but it is usually not technical reasons which hold back decisions like that. I think i just saw a post a little while back about the first mpc player coming from china - big companies like sony, panasonic could of easily come out with mpc, ogg, etc players earlier - they even held off on mp3 until they realized all the money they were losing to rio. So whether some company will take the plunge to make a mp3-4 player I guess time will tell - I wouldn't be holding my breath for it anytime soon.
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Will players require the endings ".mp3" or ".mp4" (as in Windows) or (as with a Mac) will they be able to figure out which type of file it is?
Again highly speculative - my guess is that it would use the file extention
I was curious about your filename question so i just tried some tests on my iRiver 350
the filenames are limited first by whichever OS you are using - I have Win2k so I have 127 character limit (123 characters + .mp3). You are also not allowed to have the illegal filename windows characters ie *,:,/.
the filenames are further truncated to the iRiver's 60 character limit for filenames. However they allow for your non-alpha characters ()-#& however * is an illegal windows character in a filename - perhaps the 350 does allow it but you'll have to try on another OS.
However I'm curious why you are overtly concerned with the filenames since you can put most of the information in the ID3 tags- especially if you have long filenames you can use the ID3v2 which has unlimited lenght i believe. Just not sure what you're trying to accomplish?
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Is there a list of "what is OK and what isn't" anywhere?
I don't think you will find one because;
1) It will be mp3 player dependant (as well as possibly firmware dependant) of what it DISPLAYS
2) you are really only limited by your OS as well as the format you burn the CD in (ie Pure ISO9660 - 8 characters, Joliette - 128 characters (i think), Romeo - don't know but i think its more)
3) if things are not ok you'll usually (hopefully) get a window saying not possible or a BSOD
Hope this helps you out