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Tal, if you think this is ready, I would like to get this in the upcoming releases. I believe the deadline is midnight at the international dateline, which is noon UTC tomorrow, just over 9 hours from now. 
I decided that any suggestions I might have for the non-user-visible aspects of squeezer.py and test_squeezer.py can wait for later. The best review of user-visible aspects will come from using it.
A second use of squeezer should be debugger's global and non-global('local') namespace displays. The intended format is one name-value pair per line. But values can be indefinitely large. For this, we could skip the context menu (there is not one now), use a fixed trigger of n characters, and have double-click display to a popup Squeezer View.
I will come back to this in a couple of hours to see if you have responded. I would write and merge a separate expanded news entry for idlelib/NEWS.txt.