What am I in for?

I think I'm gonna do a dex build this time instead of str. What level should I go into DLC at? Only boss I really struggled with in base game was nameless king for reference

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Start right bfore the last boss

Ariandel is FROM's worst DLC ever. However it's got the best bossfight in the entire series

Ringed City is pretty fun

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You just remind me that the ending of DS is completely shit.

is fat rolling viable in this game?

It's the most soulful way of playing.

Start both DLCs right before last boss you're saying? Or is it worth/fun to do either of them early

Go into the DLC if you're able to defeat Twin Princes.
Ashes is complete doggy doo doo but has fun weapons and some solid Pyromancy stuff to make it a lot stronger than it already was. The boss at the end is either godlike or shit depending on your disposition towards it's style. You'll know what I mean when you get there.
Meanwhile Ringed City is phenomenal, is about twice as long as Ashes, has a great final zone in the titular city and has some excellent bosses that are much more my style than Ashes boss was. It's overall the better of the two.

Dark souls 2 DLC were better, change my mind.

Sekiro DLC was better, change my mind.