In my niche of what we do, playing to tracks is almost the norm. Most of us use a program called Tracktor, it's actually a DJ program, but it has 2 decks and who ever runs the computer can load the next song in deck B and start the click before we are actually finished with the prior song. That way the beat keeps steady and the dance floor never stops. There is no dedicated click, rather the left side are all the rhythmic elements that our drummer can key into for tempo and the right side has all the melodic elements. We make efforts to create a setlist with BPM in mind so that we can accomplish this. I use Sonor and Pro Tools to create tracks. Pull in a MIDI file of the song we are doing, then I can add any part I need to recreate the original live using VST instruments.
With this program, you can have multiple views. The one that works best is the shuttle at the top, an actual .wav viewer in the middle, and the master song list underneath. You can drag and drop songs to create songlists, you can see the waveform to know how close you are to the end, and everything is right there. MUCH better than iTunes or the equivalent. Try it out, I think the one we use is $99 but you can find the program for free all over the net.