I'm 3 year-experienced guitar player, I learn from the videos and almost never use tabs. Also I'm not experienced at transcribing at all. All I could was just finding some chord tones, chord quality and a key. But as far as I go, I find that I start to recognize licks, simple chord changes, use of a b5 note, some intervals etc.
So question: Can experienced player (5-7 years) transcribe almost successfully (without particular practice) or can he make a good progress at transcribing just because he has been playing for a long time?
My point is as follows: I think that when you play a lot in a particular style, you start to recognize stuff that is being used all the time: common licks, chords embellishments and so on. For example, you hear a shred-lick and you know approx. what it could be. Or you hear a riff which is using harmonic minor, and you recognize what it's harmonic minor. But the hard thing is to transcribe all the notes perfectly, all the more if it's an interestic and unusual lick or whatever.
I'm fairly sure that it would be very useful to transcribe by yourself.