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What you are talking about is "song arrangement", and it comes not so much with practice, but with listening to music actively. Listen to your favorite track and carefully detail the structure and transitions of the song. Transitions that you speak of are part of song arrangement and are a mental discipline that should be wielded with great care.
As far as transitioning between leads on a track, that depends on the style of song that you are trying to accopmlish. Trance, for instance, is not a parade of leads and it is not always wise to split up melodies between leads without a break or so to introduce them. Of course, it also depends on the melody -- whether or not it is a motif, or a hypnotic gate, or a counter melody. It's up to your ears and your experience and know-how. There's no secret.
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...On college-driven hiatus...
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