I'd recommend anyone who's starting the whole thing to go the route i'm taking: AC1-AC3-AC2 trilogy-AC4.
AC3 did have a few spoilers for some parts of the ezio saga but nothing that'll ruin it. I'm in the middle of 2 right now and though i know where the Desmond storyline is headed, the renaissance era part is still unfolding.
Playing AC3 after 1 makes you appreciate the gameplay mechanics adjustments, various side game types, and the challenge of trying for 100%sync (I wouldn't recommend this unless you're waiting for a price-drop on the AC2 trilogy, and the release of AC4 like I was). Playing it before AC2 makes you appreciate Ezio's character even more. A bit of patience and suspension of disbelief helps too.
Also, at this point, I personally think that Connor's character isn't as lousy as Desmond.
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