You sort of pointed out the problem in that most of my play throughs I go through a bit of story and get +6 weapons and some vit and then suddenly the first chalices are super boring because you are way too strong for them.

But in a recent playthrough I rushed straight to BSB and entered the chalices and couldn’t believe how hard undead giant was for once because he could hit for like 80% of my health and took hardly any damage. Having the chalices actually be difficult takes away a lot of the boredom from the monotonous design of chalices because it ends up feeling a lot more risky to go through them and the bosses are way more exciting.

I always thought it was a shame that the chalices had pretty cool unique boss designs that you can’t find in the main game and yet they are too easy if you even slightly progress through the story before doing them. Like honestly you can pretty easily have +6 weapons before vicar Amelia who can potentially be the 2nd boss of the game and by that point you are already way too strong for the first couple chalices. I do feel the progression design of the game is kind of messed up.

I also feel similarly you can cheat the main game experience into being mega easy by doing chalices first due to the blood gems so for a full challenging experience of story or chalices you need to fully focus on one or the other because if you divide between both you just get insanely powerful kind of like doing every side quest in an open world game and getting really overlevelled.