Just as a mental exercise, thinking through bosses:
Eye of Eternity: forget it, dual boxing healers not gonna work here (flying vehicles instant reaction times etc)
Obsidium Sanctum: any would work, the raid is taking lots of AoE dmg, the main tank is taking damage. Usually run with 4-5 healers in 25 man, so could focus on MT or raid healing.
Naxx:
spider wing: pretty easy mode, one can follow the other and target the same person. No issues with Anub or Faerlina imo with any of the 4 healing classes.
Maexxna is going to be difficult since one of your guys may be web sprayed and now they are split up and may not be in range, plus you need druid healers on MT to roll HoTs.
Abom wing: You have MT and 2-3 OTs, each healer picks one and spams heal. Easy mode for any of the 4.
Grobbulus: BIG PROBLEM. If you get poison you have 10 secs to run from raid, drop it, and run back. Other healer needs to continue healing MT/raid when one is poisoned. Near end BOTH could be poisoned. Imo you are hurting the raid rather than helping by dual boxing.
Gluth: Not a big deal, both healers could be on tanks and use targetoftarget to heal whoever Gluth is currently targeting. Any healer class would work.
Deathknight wing:
Razuvius REQUIRES 2 priests, preferably with spell hit ~100 or so (holy is fine, just need hit gear). You could dual box this with some practice, would need split windows and very fast reaction times. You will probably cause a ton of wipes while learning it (lol). Other healer classes could just heal the raid and tanks, no big deal which one.
Heigan is easy, stick to one side and group/tank heal, piece o cake.
4h is tricky. 1-3 healers on first target, 1 healer on 2nd tank, another 1-3 healers in back. You have to move a lot and be "mark aware", imo dual boxing this encounter, especially healers, would be very difficult and hurt the raid more than help.
Plague wing: Noth is retard easy. Heigan is awful, you cant /follow dance since the few steps behind would mean you die. (the cheat spot will probably be hotfixed soon so ignoring that). Of course you only really need 2-3 healers on heigan so not a big deal.
Loatheb is vastly easier with a priest with CoH, of course you gotta be able to "place" it with a dual box, but not too hard. Druids are mediocore in this fight, Wild Growth doesn't have enough time to go off. Shamans are decent, can get off 1-2 chain heals during 3 sec windows. Paladins are decent MT spam healers during windows (with beacon) but you don't need more than 1 really.
Sapphiron and KelThuzad: probably hurting the raid more than helping by dual boxing, since positioning is critical in both these fights and you have to alternate between stacking and spreading out (and moving out of blizzards, red voids, etc, etc). Maybe on Saph with enough frost resist you might be ok semi-stacking, and on KelThuzad you just have to be able to move your guys independently around when people are mana bombing or void zones pop up.
Conclusion: for all the very difficult fights where healing really is important, for guilds running encounters for the first time, dual boxing healers may be hurting more than helping. Once its on farm, there are strengths and weaknesses to every class. Shamans would bring totems and lust and chain heal, pallies would bring massive healing to main tanks and beacons on melee, priests would bring crazy AoE healing, druids would bring super powerful HoTs and innervates and rezes.
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