what I would recommend is a dual player... such as clubdjpro.
http://www.clubdjpro.com/media/clubdjpro_full.jpg ((edited... the image makes the screen too wide to view normally... so click it instead!))
This would allow you to play the second file (for example, on the right player, while the left player was playing) enough to stop it at the logo... or when the song starts to play... all while queued totally on the song that's playing now. The slider on the mixer (crossfade control button in the middle upper part of the screen) would be totally on the first player (say on the left one).
I'd PERSONALLY recommend the second song be on the logo screen... that way there's NO confusion on which song the new person requested.
Anyway, when you're ready to start the second player, you just go ahead and hit the "fade now", and it will do a great segway video and music-wise where the other player slowly takes over... you can adjust this to be ultra quick, or slow... as in ten-15 seconds...
Try the demo at
http://www.clubdjpro.com... clubdjpro2 ... fully functioning demo!