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So just need a quick answer and page reference (am at work, and don't have rulebook to hand, but I need to know before I forget to check!)

Theoretical Combat.

I have three units, each of a single Sydonian Dragoon, in combat with an Ork Warboss.

If he wants to take out all three, does he

A) Just roll to hit generally, and hope for the best - if one is taken out in a single hit, the next damage roll is against the next Dragoon)

B) Have to declare his attacks before rolling to hit - If he overkills one, he can't transfer the excess to a different Dragoon, as despite being identical models, they're all separate units?

BRB p. 55 Clarifies this, under Directing Attacks in the multiple combats section. A single model can split its attacks however it wants, but it has to declare all its attacks before it rolls to hit. So, if the Warboss has say, 5 attacks, he could make 2 at one dragoon, 2 at the next, and one at the last. If his first hit kills the first dragoon, the second attack is then lost.

Sweet.

Three units of one defo the way to go.

Cheer dude (especially for the page ref, always appreciated!)

Generally speaking with walkers, that's how I run my dragoons. The only problem you run into is charges can get funky, cos each model has to roll (granted dragoons are good at that), but they can basically run into each other on the charge and increase each others charge distances if you're not careful.

Just need to keep an eye on my positioning. Plus, it means he can only Overwatch at one of them. Which is nice!

Bah. That's another NooB question. (I'm not actually a NooB, but haven't played 40k in so long as might as well be).

Charges.

Do I declare all my charges, then my opponent declares their Overwatch.

Or do I declare my charge, opponent chooses to Overwatch or not, then declare my next charge?

You resolve overwatch on the first unit charging, then roll distance and move the first unit into contact with the enemy (if possible) before going on to declaring the second unit charging.

Page 44 in the main rulebook has a handy table going through the steps in order.

If the enemy player suspects he might be charged by multiple units, he has to decide whether to use overwatch on the first unit charging, or gamble that it won't be able to reach him and save it for the second unit to charge. If he saves it and gets locked in combat by the first unit charging, he'd no longer be able to resolve overwatch on the second unit. if they were all declared and overwatch resolved first, there would never be a risk of not getting overwatch, and the player being charged would always get to choose which of the units he's using overwatch on. I'm sure GW structured it this way so that the tactical decision about using overwatch has to be made.

Pretty much as I thought, but needed to check. Because tactics!