For GPL v2 only, let's start the list with Linux and Git...
The "or later" has been used in creative ways, like relicencing all the Wikipedia content, or the Affero to AGPL transition. Nothing shady, but unexpected.
Do you trust RMS to avoid doing shady things in the later GPL licence? I do, but he is not longer in the FSF.
Do you trust the current members of the FSF to avoid doing shady things in the later GPL licence? I don't know them.
Do you trust the future members of the FSF to avoid doing shady things in the later GPL licence???
Section 14 of the GPL says "The Free Software Foundation may publish revised and/or new versions of the GNU General Public License from time to time. Such new versions will be similar in spirit to the present version, but may differ in detail to address new problems or concerns." Given that the preamble to the GPL explicitly says "the GNU General Public License is intended to guarantee your freedom to share and change all versions of a program--to make sure it remains free software for all its users", I don't think that a judge would find that a hypothetical GPLv4 that was basically MIT or something is "similar in spirit" to the present version.
If you're worried about the other direction (i.e. a hypothetical GPLv4 that had some bizarre restriction like "all users must donate to the FSF"), the "or any later version" means that as long as you don't decide to update the license you use yourself, people can continue to use it under the GPLv2 or v3 indefinitely.
The "or later" has been used in creative ways, like relicencing all the Wikipedia content, or the Affero to AGPL transition. Nothing shady, but unexpected.
Do you trust RMS to avoid doing shady things in the later GPL licence? I do, but he is not longer in the FSF.
Do you trust the current members of the FSF to avoid doing shady things in the later GPL licence? I don't know them.
Do you trust the future members of the FSF to avoid doing shady things in the later GPL licence???