His videos appear to always showcase a well-chosen example...
That is absolutely correct, and on purpose. In one of his I.B. webinars, he answered a question specifically on that. If I can paraphrase: "I prefer to focus my sharing on the few home runs that worked well, than on all of those boring ones which got stopped out uneventfully." You either believe it or you don't, of course, but it's not unreasonable: you want to learn to duplicate what works, and especially since in his style stops are systematic, only the entry and profit targets are discretionary and thus have a learning curve.
I think he did have a few losers in one of his I.B. webinars somewhere, to illustrate his money management style, no idea which one it could be though.
3 consecutive examples of the entries being annotated and commented in real time would carry a lot more weight than this cherry picked stuff.
While I have not paid to witness it first-hand, my understanding is that this is what goes on in his live morning sessions.
Very often you read that you want to see how a trader handles the losing trades. Now I'm not stupid enough to waste time going through the videos to look to see if he mentions any of these, but it would be important to note what he does in cases like this.
He stresses money management in all the content I saw. Every scenario for the trade is planned for before it is entered (including writing off the stop-loss, which is good psychology) and even for his usual winning examples he details the losing scenarios as well at every point, at least in the webinars. (Those YouTube clips are excerpts from his chat room and seem to be much less complete.) His losses are straightforward: either the stop gets hit immediately or nothing happens within a predefined set of bars (say 5-6) and he cancels/exits.
What I learned from having watched and read pretty much everything he's ever freely published, is that he gets highly in tune with specific markets (something one can only learn from screen time, not really from him), and that median lines are only a secondary visualization tool for him, for example to suggest interesting scaling out targets. Most of his core decisions seem to be actually based on horizontal lines (drawn in or implied), and let's keep in mind that a Modified Schiff Median Line is actually a normal trend line (joining A and C) with an opposite parallel (at B).
I do enjoy his narrative of the recent past as he reaches the right edge, with his "where are the positions now?" and his recommendation that traders "slow down" and think trades through. (Better to miss one than to act carelessly.)
