You do have some odd ideas, it is said Jesus never laughed, where was that said. Not that I think he ever existed as The Christian faith believes.
Happiness is not an obstacle, it is the means and the way to find contentment. No man or woman can expect more than that. Sure you have to experience life's ups and downs to think about life, and perhaps philosophise well, that does not mean it is an obstacle only that it is a goal to the wise man. Every person surmounts their mountain, and every person lives on that peak, but after the summit there is the track back down, to expect happiness all the time is naïve, to have it at all is golden. Cherish it, but also cherish sadness, it teaches us perspective, just as being wrong teaches far more than right, the sad moments teach us how much of a victory happiness is. In short no it is not an obstacle any more than sadness is, it is as it is.