FWIW, I am +1 on dropping tkinter interface.  Tkinter window looks
foreign next to browser and server-side GUI that opens a new client
window with each search topic does not strike me as most usable
design.  Furthermore, I just tried to use it on my OSX laptop and it
crashed after I searched for pydoc and clicked on the first entry.
(Another issue is that search window pops under the terminal window.)
I think Tkinter interface to pydoc may make sense in IDLE, but not in
the main pydoc GUI.  If the equivalent functionality is available in
the browser (preferably in the style familiar to docs.python.org
users, I don't see why we need to keep old GUI and hide new behind a
new option.

I agree.

What do you think of having a "-i" command line option to enter an interactive help session directly from the command line.

This is easy to do. The instruction when entering and leaving need to change a bit, but that isn't hard to do.

Cheers,
   Ron

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