As can be seen in that list, sometimes using help will result in getting multiple attacks in on the owlbear, because the owlbear misses. So it's objectively more beneficial to keep using help, however tedious it is. The choice is to do a tedious thing that will help you eventually win, or consciously lose out on a source of damage for the rest of the fight without any tangible benefit. If the only benefit to not helping is that you don't have to engage with an annoying mechanic, and not helping could potentially cost you the combat, because now you're down a damage dealer and the owlbear is likely to turn its attention to another target, then the mechanic itself is bad and needs some kind of alteration.