Do I have to upsize wire for a long run?

Ampacity tables do not care about distance, so you size conductors for ampacity first. But voltage drop is a separate check (NEC informational notes recommend 3% on branch circuits and 5% total), and on runs longer than about 75–100 ft you often need to bump up one wire size to keep voltage drop in range. Use the voltage-drop calculator alongside ampacity sizing to confirm.