MIGHT INCLUDE SPOILERS?
How to get doctor on your hitlist and his item
Before starting: You'll need to have known about Spine's secret in a previous playthrough. If you found out about it during the time you have the doctor in your hitlist, you won't have enough time.
To get him on your hitlist: Even if you haven't gotten the blackmail from any of the previous playthroughs you can still get him on your hitlist. (I still highly recommend knowing about the secret first.)
Do whatever choices you want until...
-Follow Spine
-I wanna stop you
-Run (if you don't pick this, then you'll just fail the playthrough cause you didn't have enough time)
Choose punch until knocked out
After that you just do whatever choices you want and you get to the list of characters that you can go after.
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To get his item: You can choose him first or after practice (like me)
the choices go...
-It's about Satomi... (you need to know about that one secret of theirs or you won't have the option)
-Search desk
And then you get it