The gig economy is characterized by short-term contract work completed by independent workers who are paid to perform "gigs", and who have control over when, whether and how they conduct work. Gig economy platforms (e.g., Uber, Lyft, Instacart) offer workers increased job opportunities, lower barriers to entry, and improved flexibility. However, growing evidence suggests that worker well-being and gig work conditions have become significant societal issues. In designing public-facing policies and technologies for improving gig work conditions, inherent tradeoffs exist between offering individual flexibility and when attempting to meet all community needs. In platform-based gig work, contractors pursue the flexibility of short-term tasks, but policymakers resist segmenting the population when designing policies to support their work. As platforms offer an ever-increasing variety of services, we argue that policymakers and platform designers must provide more targeted and personalized policies, benefits, and protections for platform-based workers, so that they can lead more successful and sustainable gig work careers. We present in this paper relevant legal and scholarly evidence from the United States to support this position, and make recommendations for future innovations in policy and technology.