Uhh, what was he doing at the gambling den of all places in the first place if it was just on a whim then? It's far more likely he went there for that very purpose, and that only the involvement with Rivalz game was on a whim. In any event, perhaps it is a stretch to say each and every, but it's an even bigger stretch to not say this is his core being, his primary mindset that utterly dominates who he is for the most part and one where he will completely ignore if faced with the well-being of others which occurs quite frequently thanks to the life and choices he's made, and I think you're avoiding the problem completely by speaking of what might happen then what could happen.
Yes I can agree that circumstances could change things in
any direction, not just the ones in which everything would conveniently fall into place in order for your scenario to work. It's not a sound assessment if you depend on only future developments in order to solve your problems, especially with a show that can go in so many different direction or has so many different plot twists as well. We have to measure it's likelihood based on the context we are given with, so I'd rather you try and fit the possibility into how it can happen now rather then leave it up in the wind. I've argued the same argument you have before, that this wasn't a healthy lifestyle for Lelouch to be leading and that he some how needed to learn to think about his own happiness at times as well before he ran himself into the ground and that would have made nobody happy in the end. But I took his character head-on in that regard, using comments and circumstances in relation to other characters that I hoped would help him realize he did matter, Rolo and his potential romantic developments being among them. And that is why I believe you're own assessment lacks substantial backing in order to make it convincing, you can't avoid a problem and just wait for it to be resolved, if you want to convince people you have to deal with it yourself, like Lelouch said in episode 19 to the rest of the Order about creating their own country.
Oh and I think I basically answered all your points, the gambling up above this post and how it is actually far more likely he was getting ready to destroy Britannia versus traveling all the way to a gambling den and hanging around there even though he was a student just to happen on this particular game with Rivalz. Then there was the festivals where he gave in for the sake of Nunnally whose happiness was paramount over his own discomfort, and as for nobles he also often goes to save those being bullied by them at the same time wouldn't you say?
