Going Cobra > Pursuit of happiness - Try starting pursuit of happiness right at 5:45 in cobra. That's right where the outro starts, and there isn't much activity in the track itself. User your low EQ to remove most of the low end from pursuit of happiness. Count bars - Right at the beginning of the 9th bar you can either cut straight to Pursuit of happiness (Using the crossfader or the volume faders). It may even sound good to keep it playing over cobra until 45 seconds in when the supersaw starts.

The key to not choppy transitions is introducing the next track and letting the listeners ear get used to it, then also letting it build to a point where the it won't sound like a hard cut. TBH pursuit of happiness doesn't really have this until the build.

Basically it's just gonna require practice, and learning to recognize when a song is going to build and move around enough or give you a build to let you transition out of the other song without the listener noticing.