If you take all henchmen, the game is almost too easy, simply because if everything is AI controlled you can predict what's going to happen every step of the way. I've found playing alone to be the more effective method of devising strategies because nothing ever changes. I think at most it took me three goes of Elona Reach to find the most time-effective route (an hour's gameplay), and a couple of attempts for the Ring of Fire missions. My build isn't anything special (I'm a Mesmer primary, certainly none too hot for PvE play, especially with henchmen) and I'm hardly a master strategist. I'm a bad chess player, couldn't complete the normal campaign of Advance Wars 2, and haven't won a single multiplayer game of Warcraft III.
I do agree that checkpoints need to be added to the missions. However, to suit, I also think the difficulty should be ramped up astronomically, more bosses should be added to the game (the Iron Man is the only boss fight in Guild Wars, and he's a pushover) and monster groups should be more diverse, packing dual-classed opponents with competent builds. It's a bit late in the day to be suggesting this, though. Maybe for the expansion.
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