Although I've been in vajrayana for four decades, I've experienced crazy wisdom (yeshe cholwa first hand with only one of my teachers. This could be because authentic crazy wisdom is rare and also, perhaps it is only displayed for those who can benefit and not everyone?
Here are two teachings on crazy wisdom from from Traleg Rinpoche and Khenpo Tsewang Dongyal. As usual, you're invited to comment and offer your own understanding and experience in the comments below. —Editor
Traleg Kyabgon Rinpoche: Crazy wisdom, as I understand it, means you're not confined either by your own egoistic ambitions and things like that and the spiritual ambitions on others. These two can collide. Crazy wisdom is neither sanity nor insanity. From both these points of view, what one does is termed crazy because it's not acceptable to one's point of view. This is a third perspective (laughter) that's the thing [problem] (laughter).
Q: What is the perspective of crazy wisdom?
A. When we hold a spiritual point of view, we can be bound by it and when we hold a materialistic point of view, we can also be bound by it. There are all kinds of dualistic ways of being bound. [Crazy wisdom] is like leaping into an abyss, but it's not the abyss of nihilism or nothingness.It is a leap into the ultimate state of being. This is where points of view no longer matter to you and you become a crazy yogi.
Q: So, does anything matter to a crazy yogi?
A: A crazy yogi still notices everything, while not taking anything too seriously. I think that's the point. I'm not saying a crazy yogi is totally indifferent. What I'm saying is that a crazy yogi will be just as comfortable doing something materialistic as with doing something spiritual, whereas a spiritual person may not be comfortable doing something materialistic and may feel some guilt about it. Similarly, a materialistically minded person may view the yogic point of view as totally unrealistic. But the crazy yogi (laughter) can juggle... can hop from one stand point to the other... Something like that.
Source: Video Traleg Rinpoche on Chogyam Trungpa Rinpoche, Crazy Wisdom, & the Mahasiddha Tradition. https://www.youtube.com/watch?v=Cun4xkvoSlo
Lightly edited by Lama Dechen Yeshe Wangmo.