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Your question is pretty vague and overwhelming, but, when it comes to how tracks are built, here's what I do:
Assume that every song is built the same, depending on genre obv. I mix mainly house, and there are always a couple of 'standard' builds for each genre.
What I do is instead of remembering how each track is built, I remember the standard builds (and there are only so many). And if I don't know how any specific track is built, I assume that it follows a certain standard, and I use that. If for whatever reason it turns out it doesn't follow that standard, I remeber it as an exception.
In my head I categories my tracks to the standards, and I remember the exceptions. This makes it easier.
Also you only really need to know the lenght and structure of the intro, the break and the main part. Every other part are built the same way as any of those part. The outro for example, are most likely the same as the intro, only reverse. And if it isn't, it's just another exception.
But to your acctual question. When to drop a track in?
When it sounds right. Some transitions sound good only if you loop the final 16 bars of the first track while slowly bringing the other track in over the course of 4 or so minutes. With some transitions, a mash-upy kind of aproach sounds better.
This is just something you have to figure out. It's part of your own personal style, noone can tell you how to do it. We can give you tips of course, but at the end of the day, you end up choosing among the tips as well.
It's about the flow and the energy, the harmonies and the rhytms. Some tracks just doesn't go well in their main parts, but their outros and intros mix extremely well. Some tracks just complete eachother to the extent that you can just play them side by side front to back without even EQing.
Every mix is different
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Check out Crossfade Collective
Sebastian Zander - Hotel Chaplin
Sebastian Zander - Set Two [Electro/Tech House and Trance of some sort]
Paulo Da Costa - AVGN [Prog. House](128kbps])
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