If it should be as seamless as possible I try to find 2 songs that keymatch, then I bpm match them. I look for a intro outro section in the song where I can easily EQ the bass off one track down to bring the bassline of the other track in, then for some tracks I need to re-EQ the mid or highline to make it work.
It comes down to 2 things:
Know your music in and out. Start with a collection of 50 songs.
Practice, practice and practice.
I can only remember that it took me long to get there, now I have been doing it for 20+ years some things come totally natural where someone says “that was just awesome” and I do not even think about it. So experience is really the best thing in my opinion and why I am still in the game, because basics I have done and can concentrate on cool stuff.
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