I've killed all the bosses in the main game (leaving the true ending boss for when I'm ready to move into NG+) so I've been spending a lot of time in the Chalice Dungeons. I can say that there is no doubt that the toughest content in the game can be found there. The level design leaves something to be desired, but the enemies themselves (many unique to the dungeons) can be quite a challenge once you start dipping into the depth 4 and depth 5 dungeons. The enemies can one shot you just as easily as the bosses.
The bosses in the Chalice Dungeon are on a completely different tier from the stuff in the main game. There are plenty of tricks that can be utilized on the bosses in the main game and the same can even apply to the starting Chalice Dungeons, but I feel I've reached the point where the bosses are now on par with the hardest stuff that Dark Souls 1 and Dark Souls 2 had to offer. Trying to end the boss fight quickly by rushing in with a flurry of attacks is no longer valid. Being careless and greedy with your approach can now end with the boss one shotting you. Summoning is pretty much impossible (there is a lot of setup involved to get someone into your dungeon) so you need to do it on your own.
I recently beat the Abhorrent Beast and the Defiled Watchdog of the Old Lords. I feel that those two bosses in particular are an excellent example of the patience, planning, and execution required to take on these bosses. I'm pretty happy now that they're gone and I'm ready to see what else the game can throw at me.
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