Enhancement request.  Feel free to split into separate requests, if you
think that's appropriate.  To me, all of what I suggest is related.

1. Bind `M-:' to `pp-eval-expression' by default, not to
   `eval-expression' - makes the input reading better and the output
   more useful.

2. Add keymap `pp-read-expression-map' (or similar).  It binds keys for
   `lisp-indent-line', `lisp-complete-symbol', `indent-sexp',
   `eval-defun', and `indent-pp-sexp'.

3. Define and use `pp-read--expression' instead of `read--expression'.
   (Only difference is that it uses `pp-read-expression-map'.)

2. Add option `pp-max-tooltip-size', so commands `pp-eval-last-sexp' and
  `pp-eval-expression' can optionally show output in a tooltip, and
  control its size.

3. Add options `pp-eval-expression-print-length' and
   `pp-eval-expression-print-level', which act like `print-length' and
   `print-level', but only for pretty-printing.  (No reason to suppose
   that the same values are appropriate for general printing and for
   pretty-printing.)  See definitions below.

4. Redefine `pp-display-expression', to do the following:
   a. Respect option `pp-max-tooltip-size'.
   b. Use no `emacs-lisp-mode-hook' or `change-major-mode-hook'.
   c. Call `font-lock-fontify-buffer'.
   d. Provide undo to buffer OUT-BUFFER-NAME.

5. Redefine `pp-eval-expression' to do the following:

   a. Add optional args, corresponding to prefix-arg behaviors.

      `INSERT-VALUE': non-nil (non-zero prefix arg) lets the command act
        the way `eval-expression' acts: inserts the result in the
        current buffer.

      `SWAP-TOOLTIP': non-nil (zero prefix arg) swaps the behavior
        defined by `pp-max-tooltip-size': if option says use tooltip
        then don't, and vice versa.

   b. With no prefix arg, respect `pp-max-tooltip-size'.  If tooltip not
      used then if value fits on one (frame-width) line then show value
      in the echo area.  Otherwise, show it in buffer `*Pp Eval
      Output*'.

   c. With negative prefix arg, print string values with "...".  With
      positive arg, omit the double-quotes.

   d.  Respect options `pp-eval-expression-print-length',
      `pp-eval-expression-print-level', `pp-max-tooltip-size', and
      `eval-expression-debug-on-error'.

6. Redefine `pp-eval-last-sexp': Same as `pp-eval-expression' wrt
   optional args `INSERT-VALUE' and `SWAP-TOOLTIP', and options
   `pp-eval-expression-print-length', `pp-eval-expression-print-level',
   `pp-max-tooltip-size', and `eval-expression-debug-on-error'.

The code (`pp+.el') is attached.  It's offered as is.  If it's generally
acceptable I can provide a patch.  If not, then please consider doing
what's requested in another way.


In GNU Emacs 26.3 (build 1, x86_64-w64-mingw32)
 of 2019-08-29
Repository revision: 96dd0196c28bc36779584e47fffcca433c9309cd
Windowing system distributor `Microsoft Corp.', version 10.0.19043
Configured using:
 `configure --without-dbus --host=x86_64-w64-mingw32
 --without-compress-install 'CFLAGS=-O2 -static -g3''