All of this is good advice, although if you want a little bit of a shortcut here is a "cheating" technique I've used...
So you know when you want the drop of the second song to come in, right? Listen to the second song and count the number of beats from the beginning of the song until the drop. It'll probably be a multiple of 32. Then, once you have that number, pull up the waveform for the first song and count that many beats BACK from the point where you want the drop of the second song to hit and drop a cue point there.
This way, when you play the first song, you'll know to press play on the second song as soon as you see that cue point.
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