I would consider the season a success, yes. To me, all you can do is try to get yourself in the position for the tournament. From there it's a series of coin flips. You yourself seem to recognize this, but those dang human emotions get in the way, which is fully understandable.
Last time the O's made the WS I was 2 years old, which I obviously don't remember. So I get it. But I fully believe "success in the post-season" is largely something that can't be controlled in any meaningful way. Try to have a good bullpen, that's about the best suggestion I could make.