ME1: Bring Down the Sky. It's worth seeing to the end and has an amazing sky box if you're into that kind of thing. Play this before wrapping up the story.
ME2: Get the Zaeed and Kasumi packs if they're not included. It's a shame if you're playing the trilogy but aren't bringing in all the characters you can. Also, Kasumi's loyalty mission is well worth playing and also includes one of ME's most impressive vistas. Play this during the main part of ME2 when you're doing the loyalty stuff.
ME2: Overlord. It has a very dumb vehicles section but once you're back on foot it has some very cool twists on the visuals and I feel the end of Overlord is, perhaps, more impactful than Lair of the Shadow Broker's end. Play this whenever. I think it makes most sense during the main part of the game; well before the end.
ME2: Lair of the Shadow Broker. Overall, I think this is the most impressive piece of DLC produced to date; your milage may vary depending on how much you care about the core character. Play this either very late in ME2's story or after the story wraps up; it connects nicely with ME3.
ME2: Arrival. I don't think this is well put together, but it sets up the introduction of ME3. Play this after you've wrapped up the story line of ME2. For role playing purposes I'd even suggest to play this as the last piece of ME2 content.
ME3: From Ashes. Get this early to get the most out of this character. In the grand picture I don't think he is that interesting as a character but there are some fun chuckles here and there and he also brings a unique insight into Prothean culture. Play it early in the story line.
ME3: Leviathan. Very well put together for what it is, but I don't think it reaches the heights of Lair of the Shadow Broker. Play this at least before wrapping ME3's story line up.
ME3: Omega. Get this if you like Aria as a character or otherwise care about Omega as a location. Play it before wrapping up the story line.
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