I think you are spot on with Gascoigne. I remember finding him so much tougher than the Cleric Beast (which I already found tough — Bloodborne was my first Soulsborne game). I must have tried to kill Gascoigne 20 times before he fell, haha.

You are right that he’s something of a watermark from a gameplay point of view; once you reach him, he’s essentially testing everything you’ve learned (or should have learned) up until that point. I think there’s this implicit message of “if you can’t beat this guy, you’ll find the rest of the game impossibly difficult.”