From Seasons 22 through 40 I was stuck in IV.38. I finally won, got put into III.10 and was relegated the next year. I was in League IV.2 seasons 42 through 57 before winning and moving into III.13. In my first four seasons in this league I had to win a relegation series to stay.
I was about to quit and thought, what the heck, I'll give it another shot and made the semis. I figured that would be my ceiling. A bit scared to hit league II.