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1.) It doesn't ,matter on what phase you start to beat match.
2.) If you push cue button on the player, that plays tune that you are going to drop, it will return to the 1 beat you cued. So if push play again, it will start from 1 beat.
Now if you want to do transition you described, you will do the beatmatching then press cue (track will stop playing in your headphones). Now you have to press play 2 phrases before outro. Use jogwheel to sync both tracks, and do the transition (using eq, crossfader etc).
3.)Yes, if its beatmatched then its beatmatched. But you have to be ready to use jogwheels to sync tunes, becouse for digital cd players its almost impossible to do 100% perfect beatmatch. For long transitions you have to sync tunes every 10 seconds or so.
Have Fun!
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