Large language models demonstrate limited capability in proficiency-controlled sentence simplification, particularly when simplifying across large readability levels. We propose a framework that decomposes complex simplifications into manageable steps through dynamic path planning, semantic-aware exemplar selection, and chain-of-thought generation with conversation history for coherent reasoning. Evaluation on five languages across two benchmarks shows our approach improves simplification effectiveness while reducing computational steps by 22-42%. Human evaluation confirms the fundamental trade-off between simplification effectiveness and meaning preservation. Notably, even human annotators struggle to agree on semantic preservation judgments, highlighting the inherent complexity of this task. Our work shows that while step-by-step simplification improves control, preserving semantic fidelity during extensive simplification remains an open challenge.