Hi, just my thoughts here as an untrained musician.
There'll always be chords that you won't be able to play, or that you won't be able to play unless you prepare first. So when playing with a band who's improvising there'll always be that moment when, although you know what the type of chord is played, and where it is, you still don't know where to put your hand... and decide to play a dumbed down form of it instead.
If you're talking about playing fancy chords, then the more notes to the chord the more different ways there are to play that chord. So it's not like basic major or minor chords; where you can assume that through lots of general piano playing that you will just eventually build up the muscular memory to play whatever inversion is needed. But for complex chords something memorisation must be needed?
It isn't often that I play jazz so if I don't list interesting voicings that I come across, then I will forget them forever. So I've decided to make a list of chords. The hope for me is that if I keep expanding this repertoire of chords, that sooner or later when some fancy chord is played by someone, that I'll know exactly what to play myself... even if it's a different inversion. And if one needs to be able to play such fancy chords that are in a sharp key, then it's all the more reason to have a chord repertoire; as it's easier to lose your bearing in a sharp key.
I don't intend to eventually be able to play hundreds of different chord permutations. I just feel that it helps my confidence on the instrument if I can be a master of my own limited stock of fancy chords. Anyone else here have a chord repertoire?