There are many ways to do this. You can manipulate beats per measures....so maybe the last measure of song one is 17/16 for example. When you see those old film scores with crazy meters all over the place it is usually just the composer lining up hits in the picture.
Another way is "Set Measure/Beat at Now". It will change your tempo so you will probably want to have a tempo inserted at the beginning of the song and the same tempo inserted on the last beat of your first song. It will change the tempo from the last tempo change. Then on beat one of the second song insert your new tempo.
You could divide the project into 3 files, working on each song separately. Export your final mixes and create finale file with just the audio, you won't need tempi or measures lining up, just place the audio using the Event List.
You can use "Fit to Time" at the end of one song.. that is a trickier way, but you better know how that works.
I work on videos all day long in Sonar with the same issue. I can have up to 20 music cues in a 10 minute segment and with a little thought and practice it becomes easy. It is hard to say which is the best method as every situation could use a different trick for best results.
What really helps me is I was doing this before computers. Understanding how to manipulate tempi and beats to hit Time Code makes doing it on a computer very simple.
Good Luck