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Just thought of two character builds I'd like to play:
1. Oracle. Angel path with spellbook merge. Life mystery (to be the best healer possible in the long run). Might chose the Lone Strider archetype for more mobility (at the expense of a couple mysteries; would hurt a bit early on, but wouldn't be an issue later).
2. Witch. Trickster path, aiming to learn that trick that adds a Wizard spellbook. Build might have some healing focus, with probably the Mercy patron (for Inspiring Recovery and Mass Heal).

So, which of these characters should I try playing first?

(I've only played a bit of the game to get a feel for it, and was playing an Unsworn Shaman, only just reaching the first opportunity to rest. One thing: I don't recommend choosing Slumber right away, as many of the enemies in the first area with enemies are immune; maybe wait until you start fighting demons?)
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dtgreene: Just thought of two character builds I'd like to play:
1. Oracle. Angel path with spellbook merge. Life mystery (to be the best healer possible in the long run). Might chose the Lone Strider archetype for more mobility (at the expense of a couple mysteries; would hurt a bit early on, but wouldn't be an issue later).
2. Witch. Trickster path, aiming to learn that trick that adds a Wizard spellbook. Build might have some healing focus, with probably the Mercy patron (for Inspiring Recovery and Mass Heal).

So, which of these characters should I try playing first?

(I've only played a bit of the game to get a feel for it, and was playing an Unsworn Shaman, only just reaching the first opportunity to rest. One thing: I don't recommend choosing Slumber right away, as many of the enemies in the first area with enemies are immune; maybe wait until you start fighting demons?)
I recommend to play in order as you listed them.

Simply Angel path before Trickster Path.

The main reasoning behind that is, I really like every path the game offers. And after seeing all of them, I think Trickster is best to be played after Angel/Demon path, so you get at least a good idea of whom you play "a trick" to enjoy it more.

Aside of that, you can play like you want. The reasoning is just based upon the assumption you are going to play both anyroads. The game is genial when it comes to single playthrough experience, so the choice does not really matter on the long run.

Trickster is just the kind of type, which benefits from knowing more about the game already.