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Should I play Dark Souls original or Remaster?
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Dark Souls 1 is 100% worth playing. I won't be a purist and say that you need to play it before 3, because they're mostly standalone experiences... but you might miss a handful of references if you play 3 first.
As for how to play: if money's not a question, buy the remaster -- you'll get a better online experience that way.
If you're on a budget, however, you could simply Install the DSFix mod and start playing with the adaptive controller as-is. There's unfortunately no in-game rebinding UI, but you can still do remapping using either the Xbox Accessories app or directly in the Steam overlay (requires Steam to be in Big Picture mode).
I'm giving the first another shot with DSFix because I am a cheap ass, haha. So far so good. Definitely a little different learning curve but it kept my ass up until 3am playing. Managed to get to the boss on the bridge with the mallet. He flattened me after the archers spammed me to death. Good times.