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I've always had a latent interest in Guild Wars, but with WoW and school winding down, I'm really looking at getting it. But, I'm not sure what box to buy (first). After a couple quick scans, the price differences are negligible (like $10-15 between the first and newest boxes) so that didn't narrow my choices down any.

I played one of the free Factions weekends and Assassin was pretty fun. I also like playing healers, preferably not the "omg squishy" type though (in case either Factions or Nightfall provides something along those lines).

So... any help?

I'd recommend Nightfall.  It's just a better constructed campaign.  The Ritualist and Assassin are good professions, but so are Dervish and Paragon.

In fact, a Paragon is a very non-squishy support type class, so might be just what you're looking for.

What Llava said. I'd pick up Prophecies eventually because there are some bread and butter elite skills (Sinister Strike) found only there to my knowledge but the quality of design is noticably lower.

Friend and I were considering getting into Guild Wars for some kicks. How does the expansion work exactly? Can I buy just an expansion and play that way, and if so what content is and isn't available to me?

I love the causul PvP of Fort Asphenwood, so I'd say Factions for me.  But for PvE I'd say Nightfall.

Each expansion is an independent game. You will have access to the  PvP island chain, and you can purchase or trade with players to acquire weapons from parts of the game you do not own, but you cannot acquire skills or armor from the other portions of the game... nor can you play in their territory.

Factions and Nightfall each give you eight classes to choose from, Prophesies only provides six. Each game has twenty or so unique skills per class available only within its territory.

I'd suggest Nightfall, the Hero's make a huge difference in doing missions.

Heroes.

Thanks.