Do One-For-All users have different training experiences?
Yes, the other successor's for One-For-All where handpicked by the previous users among the most fit to use the quirk. Gran Torino mentions that even though Toshinori/All-Might was born quirkless, he possessed great resilience and endurance to maintain One-For-All power.

Midoryia had no previous training nor did he had good constitution or muscle strength to keep up with One-For-All's great stress upon the body. That is why All-Might has those often remarks about him.