Rogues in Concert

[sjeshin]

I am looking to get a consensus from some more experienced DM's than a RAW does or doesn't, but a RAW conclusion would also be appreciated.
I am trying to figure out if two rogues, working together, can have one of them ready an action to move from cover and attack at the same time the other one does.

My intended outcome, its both rogues run out at the same time, flanking the target, and then attack with their sneak attack.

Looking at the ready action section in the PHB i'm not sure if this pans out. I'm looking to use it more as the DM, with a "kill team" / "assassins" going after the party, but since I play more than I DM, I really don't like to use things Players can't do as well.

Would the majority of DM's out there allow this to work regardless of RAW? or is it in line with RAW?

[Emperor Tippy]

Yes. Whichever one has the higher initiative goes first, using a move action to take their position and then readying an action to attack the enemy once the other Rogue is in position. The other Rogue moves to take his position and then attacks as normal.

[FinnDarkblade]

They don't actually have to flank the first round if the players don't know they're there. Any character that doesn't have uncanny dodge will be flat-footed due to it being a surprise round.
*edit* Although this does bring up the problem of only getting a partial action during the surprise round.

If they're high enough level to have access to invisibility then you could have them take up flanking positions before the surprise round even starts. That way they could both get SA's during the surprise round and if they win initiative they both get full-attack SA's.

[Chronos]

Surprise round, they hopefully both get surprise, and charge in for Sneak Attack due to enemies being flatfooted. First and subsequent rounds, they take 5' steps if necessary to get into flanking positions, and full attack for more sneak attack due to flanking. If they're not quite in position yet for the first round, they probably still get Sneak Attack due to winning initiative. No readied or delayed actions are necessary at any point.