Prioritize reliable inter-island carrier schedules, proofed WMS integrations (APIs or EDI), on-site handling and temperature-controlled capacity, SLA guarantees for pick-and-pack, and transparent billing. Also assess transfer times to main population centers and contingency plans for seasonal weather disruptions.

Compare total landed cost per SKU including feeder freight, handling, and last‑mile delivery versus mainland consolidation savings. Model lead times, buffer stock needs, and service penalties. Use historical carrier schedules and volume tiers to stress-test cost sensitivity under peak season traffic.

Verify dock and quay access windows, forklift and pallet racking availability, cold-chain monitoring, WMS functionality (real-time inventory, batch and expiry management), and integration options for order routing. Confirm labor skillsets for returns processing and kitting too.

Look for defined contingency clauses covering carrier cancellations and weather delays, scalable space and labor provisions for seasonal peaks, secondary pickup options, and clear KPIs for fill rate and on-time delivery. Consider multi-location redundancy and periodic disaster recovery drills.