For myself, I only want this for 'large' outputs.  I prefer something like the following left alone.

>>> help('continue')
The "continue" statement
************************

   continue_stmt ::= "continue"

"continue" may only occur syntactically nested in a "for" or "while"
loop, but not nested in a function or class definition within that
loop.  It continues with the next cycle of the nearest enclosing loop.

When "continue" passes control out of a "try" statement with a
"finally" clause, that "finally" clause is executed before really
starting the next loop cycle.

Related help topics: while, for

The threshhold for squeezer should be good enough.  I think of this as autosqueeze + autoexpand if this if the first output after '>>>' and the statement began with 'help('.  An advantage of doing it this way is that the squeezer button remains after dismissing the viewer.

Also, I suspect that most people who disable squeezer would not like this either.