What do you check before trusting an airport-to-hotel route?

A practical travel question about luggage, payment, late arrival, and final station exits.

Airport-to-hotel routes look simple on maps, but the risky parts are often baggage claim, ticket payment, elevator access, late-night service, and the final walk from station exit to hotel door. I usually check the first transport payment method, whether the station exit has an elevator, whether rain changes the final walk, and what the taxi fallback is. For a first night in Seoul, Tokyo, Bangkok, or Singapore, what do you always check before trusting the route?