Although Decibel has problems of its own, one thing I'm avoiding for streaming like plague is iTunes. I do use iTunes to organize my tandas, but even there I wish I had started out with a more sensible piece of software (now I'm kind of locked in, as iTunes does not support exporting playlists and playlist folders en masse).
Here is one of many reasons why to avoid iTunes as a primary streaming device: occasionally, with some regular mp3 files iTunes plays the song until a while, and then in the middle of the song it stops and jumps to the next track!
This is strictly an iTunes player issue: these files are not damaged and can be played by other media players without any problem. This is also not an issue with iTunes settings: neither the start, nor the stop times are set and/or checked for these files.
I made a screencast video to demonstrate the problem:
One things I'd like to add to the video is that erasing the file from the iTunes library (completely removing it from the database, not just from the playlist) and reimporting it does not solve the problem.
Apple has been made aware of this issue years ago on its forums (by myself and others) but so far no representatives cared to address it. Here is an Apple discussion forum that I just started (since my old discussion forum post apparently got removed): discussions.apple.com/message/28250270#28250270
If you are also worried that this might happen with you in the future, please help increase awareness of this failure of core functionality. Apparently Apple doesn't bother fixing it until enough people are expressing their worries.