> To check which Ruby the newly created vim was linked against, I did
>
>    $ otool -L vim
>    ...
>    
> /System/Library/Frameworks/Ruby.framework/Versions/2.0/usr/lib/libruby.2.0.0.dylib
>  (compatibility version 2.0.0, current version 2.0.0)

I see how your judgement is flawed here.

Take a look at
# otool -l /usr/lib/libruby.2.3.0.dylib

...
Load command 10
          cmd LC_REEXPORT_DYLIB
      cmdsize 112
         name 
/System/Library/Frameworks/Ruby.framework/Versions/2.3/usr/lib/libruby.2.3.0.dylib
 (offset 24)
   time stamp 2 Wed Dec 31 16:00:02 1969
      current version 2.3.0
compatibility version 2.3.3
...

So basically, I suppose, you have in fact linked against 
/usr/lib/libruby.2.3.0.dylib, but otool shows you the original library instead. 
Library path resolution has nothing to do with this.

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