Nobody's interested in sharing the spotlight. This is a fierce competition to be on top.
But you are onto something - any suggestions for 5E or 3E magic items that - crudely put - allows the Rogue to grant himself a Commander's Strike would do the trick.
Assuming this happens off the rogue's turn, since I'm not interested in violating the core premises here (the rule about only one sneak per turn).
This thread is about applying decades of system mastery in finding a solution that appears simpler than it might be
For example - I'm looking at something called "Kyton armor" from 3e. Maybe I can create a thingy that makes an attack on somebody else's turn, and allow the Rogue a second sneak attempt that way.
Another idea is to upgrade the parry (allowed by the feat he's got, maybe Defensive Duelist) into a riposte.
That is, using your reaction to make a counterattack on a miss. That should enable sneaking, right?
Rather than alter the feat, simply create a magic item that accomplishes this.
Say, Bracers of Backlash, that allow him use his Reaction to make an OA when hit (you might even go so far as to say attacked, that precedent has been set by the Mobility feat). That should greatly increase his chances of getting his two sneak attacks in the round...
Bracers of Backlash
Wondrous item, rare (requires attunement)
While wearing these bracers, you may use your reaction to make an Opportunity Attack against any opponent that attacks you, regardless of whether the attack hits or misses.
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