Overseas medical care is usually payable on the spot, and whether that becomes a direct payment or a reimbursement claim is settled early and rarely revisited.
People traveling for months on a fixed total describe a consistent set of rules about where to economize, and almost none of them involve finding a bargain.
Local lodging taxes, resort fees, vehicle surcharges and parking are set by the destination rather than by the supplier, and comparison sites rarely show them.
The people who pay travel claims are not the people who sell travel, and the questions they answer most often all point back to decisions made at booking.
A car rental total is built from taxes nobody can avoid, surcharges attached to the pickup location, and a handful of charges that are entirely the renter decision.
The airline, the card issuer and the travel policy each owe a traveler something different, on different deadlines. Going to the wrong one first can cost the strongest claim.