It does seem to match your issue, or it’s at least close, and the us keymap doesn’t do it. 
Yes, this is a video recording of my screen)
I only hope for an update or I’ll change the password when I get tired of suffering
since we are obviously not able to pin down the issue
which is:
you could type ‘ as a single character with one single keystroke
but now you can’t anymore
no one knows why it is different now
I’d have changed the passwd already and had been done with it.
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You might try entering Unicode codes directly.
Type “Ctrl-Shift-U” (skip quotes) then type the codes (skip = and the character after):
0027 = ’
0060 = `
00b4 = ´
…and finally press Enter.
Not sure that’ll work in a TTY though, but could be worth trying. 8)
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It seems that this does not work in TTY, since when you press control, the characters are displayed, but when you press the keys, you immediately enter something completely different from what you need (
Okay, I thought it might be problematic.
What about if you can reach the Python interpreter? You might be able to run code that can produce what you want on the command line and, if possible, maybe copy and paste them?
>>> print(chr(39))
'
>>> print(chr(180))
´
>>> print(chr(96))
`
Or create a Python script file and run that to produce the correct output.
$ nano pythontest.py
print("the characters you can type"+chr(180))
Which can be run with:
$ python pythontest.py
the characters you can type´
$
Or some other scripting language you might have.
Other than that, I’m fresh out of ideas.
Good luck.
Why the contorsions?
Simply change the password to something that can be easily and reliably typed.
It still doesn’t explain why it did work but then it didn’t anymore after some update.
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the characters you can type´ //180
type' //39
` //96
This symbol is typed from the keyboard, but only if you press any other symbol before pressing it.