Best travel insurance comparison for indie hackers

The travel insurance space has roughly 200+ comparison platforms globally, but almost none are built for indie hackers, digital nomads, or solo founders shipping products across borders. The core pain point isn't finding insurance—it's finding coverage that accounts for your actual risk profile: extended stays in multiple countries, work-while-traveling status, equipment coverage, and liability that makes sense for technical work. Most tools funnel you toward traditional expat packages or backpacker plans, both of which miss the mark for someone earning six figures remotely. The gap exists because travel insurance carriers haven't segmented the indie hacker persona as distinct from tourists or corporate employees, and comparison platforms haven't bothered building UX for that market. A new entrant should focus on three things: (1) building a comparison engine that prioritizes coverage for digital work and equipment, (2) creating transparency around visa implications and tax residency (indie hackers care deeply about this), and (3) offering a simple CLI or API integration so vibecoders can check coverage while deploying code. The real opportunity is vertical integration—not just comparing policies, but building a full nomad financial toolkit that bundles insurance with tax filing and visa tracking.