When I play guitar, together with a friend, we always have a discussion, concerning putting your fingers in a certain position. I know a significant number of chords, but I don't have "Jimi Hendrix" fingers, so some chords are not easy to take. But our discussion is always concerning chords like C D E, he takes these chords using a different setting of his fingers, and he can not understand why I take the same chords with another position, different finger setting.
Maybe he is right, but when you play at least 25 years you take the chords like it is more easy for the player. It is sometimes difficult to take chords, like Adim7 for instance. But for every even very difficult chord you can find a similar chord that is less difficult to take.
Practising is the name, and not because you have a guitar since yesterday, everyone wants to play the same day, so chord 1 then chord 2 ...
The hardest chords you will find in jazz, sometimes in blues, and to be honest, a lot of times in a song, you can try that difficult chord, but like I wanted to tell, you can skip them often. But for me the most difficult songs to play are 50 WAYS TO LEAVE YOUR LOVER (PAUL SIMON) and QUEEN with BOHEMIAN RHAPSODY, very difficult chords.