Personalized LLM systems have advanced rapidly, yet most operate in domains where user preferences are stable and ground truth is either absent or subjective. We argue that individual investor decision-making presents a uniquely challenging domain for LLM personalization - one that exposes fundamental limitations in current customization paradigms. Drawing on our system, built and deployed for AI-augmented portfolio management, we identify four axes along which individual investing exposes fundamental limitations in standard LLM customization: (1) behavioral memory complexity, where investor patterns are temporally evolving, self-contradictory, and financially consequential; (2) thesis consistency under drift, where maintaining coherent investment rationale over weeks or months strains stateless and session-bounded architectures; (3) style-signal tension, where the system must simultaneously respect personal investment philosophy and surface objective evidence that may contradict it; and (4) alignment without ground truth, where personalization quality cannot be evaluated against a fixed label set because outcomes are stochastic and delayed. We describe the architectural responses that emerged from building the system and propose open research directions for personalized NLP in high-stakes, temporally extended decision domains.