We believe this to be a limitation of the Tungsten T2 and Ogg Vorbis.
Unfortunately, the T2 has less dynamic heap memory than most other PalmOS handhelds. Our Ogg Vorbis library uses a lot of dynamic heap memory, and when you turn on crossfade, it uses 3 times as much. Unfortunately, that means that you are likely to run out of memory on the T2.
(Note that dynamic heap memory is different from what's shown in the crossfade preferences screen.)
We are looking into ways to decrease the memory usage of the Ogg Vorbis library in a future release. In the meantime, you may continue to see these types of crossfading problems. If you are able to switch to MP3 or WMA files, you will probably have better luck.