Finally found out a bit more about this: it seems to be a theme bug.
When testing Manjaro, I noticed that the context menu on initial Caja
window opening displayed an arrow at the bottom to show more options,
among which the "empty trash" one. I first thought it was because the
apps versions were different and it has been fixed on Manjaro (as it's a
rolling release version). But trying a different theme on Ubuntu MATE
like Arc shows the same arrow.

So, the issue seems to actually be with the default Ubuntu MATE theme
(Ambiant-MATE, Radiant-MATE and Ambiant-MATE-Dark), though I'm not sure
why Caja behaves differently when opening the trashcan context menu
(click once: it'll show part of the menu with an arrow to scroll; click
again: it'll show the full menu).

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https://bugs.launchpad.net/bugs/1826326

Title:
  No option to empty trash on initial window open/dir change

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