I know of a few guys that have won OL titles with each of their first three teams... I know of a couple others that did the same in theme leagues (something I find much more impressive) and one or two that won with their championships in their first 2-3 seasons in progressives...
And, to the best of my knowledge, I've won just one OL title, but that's a long story (and that was my 6th team trying to test a particular strategy that has made other famous and changed the way the site works)...
I don't usually play OLs to win, but to test various elements of the game, if I win more than I lose, that's a plus, but normally my OL teams lose more than not. They're just a good place to put the sim to the test.