LLMs can plan by either generating action sequences directly as a Planner or translating tasks into domain specific language for an external solver as a Formalizer. While most real-world tasks are asynchronous with non-uniform durations, concurrency, and execution-time constraints, existing benchmarks hardly cover them. We unify these asynchronous planning challenges under a single formulation and introduce the first three benchmarks that address each at scale. We conclude that the choice of formal representation primarily determines whether planning scales: as dependency graphs grow from 5 to 100 actions, Planner collapses from 96% to 5% plan accuracy and PDDL2.1 Formalizer from 13% to 0%, while CP-SAT Formalizer averages 94% and still achieves 83% at 100 actions. Faithfulness diagnostics show that PDDL2.1's predicate-based planning representation becomes brittle compared to general constraint satisfaction programs, when LLMs must keep predicates, effects, and goals consistent. Execution-time updates of planning constraints further degrade performance sharply (Planner 23.9%, PDDL2.1 0.7%, CP-SAT 46.1%), but a state-aware repair strategy that updates only event-induced constraints recovers CP-SAT Formalizer to 84.5%.