If I immediately let Sakura go, then there wouldn’t have been a point of catching her at all. She couldn’t stand since she drained nearly all of her chakra by helping Obito locate me in one of those dimensions. And the eye contact was nothing more than that…
It’s as I told Naruto at the Valley of the End, they weren’t meaningless. The good times I had with them mattered a great deal and had their own significance at the time. I simply had to move forward and that meant leaving a future with them behind.
It would all depend on when this happened to discern my level of care. However, no matter the circumstance, I told him multiple times not to waste his time over searching for me or anything pointless like that. If he sacrificed himself, that was his own decision, one he probably wouldn’t see as a mistake, knowing him.
Most seem to get the impression that I don’t hold an ounce of care about anything at all unless it’s about my revenge. In which case, that’s not completely true. I only became focused on that goal because it was all I had when off training with Orochimaru. Two and a half years of my life was dedicated to killing my brother.
Either way, if it occurred right after I left, no I wouldn’t have cared at all. I intended on killing him myself at one point anyway and believe that was just something out of the way now. And if it was closer to the war, I’d probably have more care.