Activate Woe Strider by sacrificing Twilight Shepherd
When Twilight Shepherd dies, its persist ability triggers, returning it from your graveyard to the battlefield with a -1/-1 counter on it.
When Twilight Shepherd enters, Stalwart Successor triggers, putting a +1/+1 counter on Twilight Shepherd
Resolve the Woe Strider ability.
Repeat.
This cunning loop turns a creature's demise into an endless cycle of rebirth by letting Woe Strider comfortably sacrifice Twilight Shepherd over and over again. Each time Twilight Shepherd returns via persist with a -1/-1 counter, Stalwart Successor steps in to place a fresh +1/+1 counter on it; these opposing counters neutralize one another as a state-based action, leaving the Shepherd completely clean of counters and ready to persist again the next time it hits the graveyard.