Once is not a large sample size. I'm sure there are plenty of cases where it would be relatively clear that with high probability they wouldn't be behind by Demo Day. For example, startups that already have been working for a while, already have a significant demo or even beta, but still need help on positioning and tweaking their product. Just set the bar higher for these startups.
Also, as someone else pointed out, travel is an option. It could be more than just the dinners, e.g. perhaps three days (two nights) a week.
Finally, I didn't mean to suggest that the opportunity missed is solely an investment opportunity. I meant more generally the opportunity to develop great startups to their full potential, which might otherwise not do so. In my case, I don't need the money at all.