Playback multiple tracks


At the moment I am considering to purchase an audio interface that comes with Cubase LE5. Since I would like to use it for a quite special purpose I first want to find out if this program will fit my needs before I buy it.
I am a complete newbie when it comes to Cubase, so sorry in advance for incorrectly naming functions, features etcetera.
Here goes: I would like to use Cubase with the interface for three things:
1: playback a clicktrack that I use during live performances
2: playback some samples at the start of a new song, and since this is in sync with the clicktrack it should make for quite a cool effect

Nothing shocking so far I guess, just a matter of assigning the clicktrack to 1 output channel and the samples to another output channel. But here is where it gets interesting:

3: in between the songs I would like to have a “backing track” running, so for example some guitar chords that prevent the stage from going completely silent. This track should start at the end of a song and stop at the start of the next song.
Off course I could simply put the “backing track” in between the songs, but I do not want to keep a fixed time between 2 songs. Also, if I have to skip a song in the set due to time constraints this will be audible. I want to be able to do stuff in the click track channel without affecting the playback of the “backing track”.
Can anyone tell me if such a thing is possible?