i've been debating this recently.  i've just gone back to regularly transcribing solos after a long (4-5 years at least) layoff due to burnout.  my ear is pretty good and i can usually go through a solo a day if i have a couple hours on my hands. (less than that if i don't stress so much about notating the rhythmically tricky parts, which i always do).  having a new solo committed to paper, i usually pick one or two tasty licks to add to my practice routine (with the accompanying harmony) before moving on to next solo the next day, keeping the written transcription for future use if needed.  i do this to keep my ears sharp as much as anything else.  

i've been asking myself this question: i've been slowly building up a nice store of transcriptions, but am i really benefiting as much from this as i could be?  i'm starting to wonder if i should slow down and really work through a complete solo until i can play the whole thing (or at least the important parts) in multiple keys so i can more thoroughly absorb it, rather than taking tiny chunks from multiple solos.
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(forgot that you still can't edit here): to put it another way, i feel like i'm picking up on lots of new approaches via osmosis, and it's showing up in my playing, but i wonder if i would benefit more from more immerse study of a smaller batch of material.
i'm partial to the osmosis approach.  things seem to stream more naturally that way...perhaps a combination of both would be cool?

to me it's like any other language.  we learn vocab better by hearing others use it.  personally when i hear a line that i think is cool, i'll practice in in all 12 keys so i'm able to play it when and if it presents itself in one of my solos
transcriptions are one of the best ways to expand your playing and as you have touched on in your post there are different ways of getting stuff out of transcriptions.

you can transcribe as many solos as you can and just move on to the next when you have one under your fingers.  this is ok, you'll get tons of ear training experience, your chops grow, and your playing goes in directions you never thought possible.

i always like to analyze a transcription after i'm done, before i move on to the next (which doesn't happen nearly as much as it should.. i'm probably going to die wishing i did more trancriptions).  

when i say analyze, i like to look at it compositionally at first.  are there themes in the solo that the player comes back to or develops throughout the entire piece?  guys like keith jarrett and pete christlieb are masters at this.  they will come back to stuff they explored in the first 8 bars and try it again in a new variation or direction... i try hard during my solos to make them compositionally sound. theme, variation, cadenzas, come back to themes and such while at the same time trying to keep it fresh and fun.

i also like to figure out precisely why certain lines grab me.  how do they fit in with the harmony?  is it a pattern of some kind that i should be aware of?  is it based on a patter and made to look like something else?  how does it fit into what came before and what's going to come next?  i really enjoy analyzing music, maybe because i love composing music.  the more musically mature i get the more in depth i analyze my own compositions and the solos and compositions of other musicians.  i'm just so curious about how things fit together.  lately i've been looking at debussy and all the amazing gospel cadences he puts in his compositions. cadences that last for like, 5 1/2 measure, or some other sort of odd timing.  can't wait until this stuff shows up in my playing.
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i just got into a kick where i'm doing a half hour of transcription every day in the morning, just after waking up.  now after a couple weeks i'm in a groove where i feel like i need to do it in the morning.  plus it gives my brain a kickstart.  it's turning into a habit, but it's one that i'm enjoying.

plus, lest i forget, that morning transcribing session is giving me a lot of musical ammo already.  too bad i haven't been doing this as regularly for the past 20 years, eh?  (saying that makes me feel old!)
If I'm not back in 24 hours, call the president.

Scot is available for skype jazz piano lessons (and google hangouts, phone call, etc...)
Use the contact link at the top of the page.
i don't transcribe. i learn parker heads...
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