Its just about experience really... Once you've got enough jam sessions under your belt things make sense. When I first started out I had to plan everything down to the measure to keep from trainwrecking because I didn't know anything about musical structure and didn't know my tracks very well. Nowadays I can just start up and mix for hours on end, and most of the knowledge I've gained was really just from random practice sessions. I'd just throw songs together and sometimes they would work. After finding the same scenarios enough times I learned why things worked and now its just natural...
So yea, out of that rambling I guess what I'm trying to say is: practice. Maybe there's a quicker, more structured way to learn, but just putting the time in works.
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