Newbie questions - 2-3 toon comp for leveling alts

[nodoze]

In a hurry getting to my work stuff but initial thoughts:

6) Is ISBoxer the best software option for me, based on the above?
- I like ISboxer even when using just 1 client for some games as the functionality is just that helpful. I definitely recommend it for 2+ clients.

5) With multi-boxing, do people quest? Or is it generally grinding mobs and dungeons?
Generally leveling via instances is an option 5boxers have with little/no overhead of recruiting team members and what not that others don't. Often the end goal is being able to farm instances at cap. A team with DPS + healing can also grind mobs well. Questing is also an option though it is typically better/faster for a 5boxer to in level instances except for certain level ranges where lots of quests are well laid out. On new servers/expansions questing and starting zones can be very frustrating to progress in (especially if PVP is active). Some quests are not great for boxing (get X of Y drops for example)...

4) Are Warlock and Hunter just bad choices generally due to the micro management the classes involve (soul shards / feeding pet etc)?
After getting the SoulSort addon I don't find Warlocks painful to manage as it keeps my soul shards to a set limit for me. I haven't boxed hunters so can't speak to that but I haven't heard pet happiness being a huge issue. I would be interested in hunter multiboxers thoughts on ammo and pets.

1) I had originally only considered duo-boxing, but now I am wondering, is running 3 toons much more difficult than running 2? (I wouldn't do more than 3, as I don't want that many subs!)
With a good tool like ISboxer I don't find running 3 much more difficult than running 2. Generally I conceptually think a decent multiboxer can run multiple toons in pre-thought-out & practiced scenarious about 80% as effective as dedicated players that listen and work well together. I find it a lot better than when grouping with unskilled people or people who don't work together.

2) Are there any good 3 toon set ups based on the above preferences which would be fairly easy for a complete newbie to all this?
Will have to think on this as most Classic/TBC teams are based on 5 boxing. As long as you balance DPS with Healing/mitigation you can go far. Note that the Hybrid Tax is much less in TBC than it is in Classic so Hybrids like Paladins, Shaman, & Druids are even more viable in TBC though Druids have a harder time doing more than 1 role at the same time due to forms and can't leverage consumables and engineering as much. Personally I plan to have Paladin+4Shaman as my main team again and if 3boxing would maybe do Paladin+2Shaman (or 3 shaman) as core team(s). If you stay with a Mage main a Paladin+Mage+Priest/Shaman/Paladin each has some merits.

3) What are the best pairs, based on the above preferences? ...
A little confused here. Are you looking for a 3 box team or a 2 box team? Hunters & Warlocks are mini-trinities (tank+dps+healing) unto themselves and can scale well by adding a 2nd or 3rd of themselves (IE 2-3 Hunters or 2-3 Warlocks) though one pain point is rezzes (though Warlocks can leverage soul-stones and both can try RNG engineering rezzes). 2 Pet classes and a Shaman is pretty nice due to Totems and the Shaman being able to switch on the fly between DPS and healing (and being able to be soulstoned, ankhed, and able to rez).