I have a mix of VBR and CBR files made in several different encoders. Have you read the FAQ entries on this subject? I'm using my own Gapkiller software to do the trimming. The behavior of the WinAmp Gapless Output Plugin and the Empeg player is very similar, so I'm getting pretty good results with it.

Now, in 2.0b3 there's that known bug where there's a caching skip just before the end of some files. But that's fixed in later builds and the behavior is back to normal, and I get decent results. Dark Side of the Moon is nearly perfect on my player except for one slight transition between two songs.