It maybe true that YC won't penalize me for applying multiple times. Like I mentioned in my other response here, I would be far more confident of applying at this stage if I had a technical co-founder or traction. W/o either of these, my case doesn't appear very strong, at least for now... and that's why I have been going back-and-forth about applying right now or not.
Also, YC fall deadline is about 3 weeks away, and I don't want to make a hasty move wrt finding a technical co-founder.
You are right - gambling does not make sense here. In the current situation, if I had either the technical co-founder, or demonstrated traction for my app, I would have been far more confident of my YC application.
If my Stanford co-founder wouldn't have scaled back his involvement recently, we were just on track to apply for the YC fall batch. Now, when he is not there as technical co-founder, the situation does becomes different. Earlier, our chances would have been good as we brought in a decent balance of complimentary skills to the founding team - we could have managed w/o traction (if I may say so). But as a single non-technical co-founder, showing traction becomes a must-have.