I for one would like to try some more boxing things as a guild. 25 man ToC would definitely have some actual upgrades for people too since it drops ilvl245 gear (above what we can all easily get from heroic badges) and would be fun and challenging.

However, ToC is pretty rough. I ran it on 5-10 toons a week for a few months, so I know the fights pretty well. I think getting past the first "boss" (trio of mini-bosses) has a number of boxer-related challenges:

Gormok the Impaler:
This guy shouldn't be terribly hard - needs two tanks taunting off one another, people to run out of fire, and everyone to focus on killing snobald adds when they spawn.

Dreadscale and Acidmaw:
Things get a bit tougher here. Need one tank on each worm the whole time, all DPS on Acidmaw till he drops. One issue will be the paralyzing poison / burning bile coordination. Acidmaw will spit poison in a small area that tends to hit 3-4 people if everyone is spread out. This will do damage and slow you, increasing the slow for 12 seconds or so until you can't move at all. If you don't get to the toon in the raid that has burning bile (something Dreadscale spits out), those who are paralyzed won't be able to move and will eventually die. Additionally, one of the worms will be pooping out slowly expanding acid clouds that may be in the way of burning bile / paralyzing poison guys moving together.
So for boxers our job would be tougher because more toons would be hit (harder to spread out boxers) by each poison attack and movement may be a bit tougher than normal.
Overall, with good coordination shouldn't be a show-stopper, but tough.

Icehowl:
The last boss is the easiest for a normal group but will present a major problem for boxers. He is solo tanked, usually with the tank's back against a wall as he does a knockback attack. About 5-6 times during the fight he jumps to the center of the arena and blows everyone back to the arena walls, stunning them for about 4 seconds. He then points himself at a random raid member and charges them, hitting them only 2-3 seconds after the stun wears off if they aren't moving away very rapidly. Every single raid member must be on their toes for this - looking at where he is facing after they are stunned and determining which direction they will run along the arena walls to avoid his charge. If anyone is in the path of the charge, he becomes enraged and one-shots anyone he attacks for about 15 seconds (killing a good portion of the raid). If someone isn't looking very carefully, they may move INTO his path right after the stun, as well as someone who isn't moving right when the stun wears off or moves at the wrong angle, etc.
When I two-DPSed this in a recent PuG, I positioned my toons near the center of the arena but about 20 yards apart on either side of the very center. That way, they were blown to opposite walls by Icehowl and I could quickly look to see who would be closer to the charge and only move that toon. With some practice (and losing quite a bit of DPS time trying to get everyone well positioned) one person could probably do this with 3 or 4 toons, but no more than that or you'd have to move two toons at once (both potentially being in his charge path) which would be dicey at best.
Most boxers tend to keep their toons together and just use /follow. I'm fairly sure that there is not enough time during the charges for follow to effectively get all the toons out of the charge path.
One bright point in this is that hunter's tranquilzing shot ability will remove the enrage, but even when this is done Icehowl has usually one-shotted at least 1-3 toons.

Those are my thoughts on boss #1.
Boss #2 should be much easier.
Boss #3 (faction champs) would present more problems.
Boss #4 should be doable (with multi-click)
Boss #5 should be doable as well.

I don't think these issues are insurmountable - we'd just have to come with a lot of patience and some gold for repairs.