Yet another reason why Inspiring Leader is a fantastic feat. There's a world of difference between an Owl with 1 HP and an Owl with 1 HP + 25 temp HP.
I don't agree with the interpretation that thinks that the "Working together" restriction on PHB 175 also applies to the "Help Action" text on PHB 192. The description on PHB 192 makes it clear that "feinting" and "distracting" is sufficient to grant your ally advantage, and furthermore, applying the "Working together" restriction to this action would make it extremely narrow--I can't Help someone hit with a longbow unless I also have a longbow? Finally, the Help text on page 192 makes it clear that you can EITHER help another creature with a "task" (same language as PHB 175, and I would apply the same restrictions) OR "Alternatively" you can help a friendly creature attack a creature within 5 feet of you (even if the friendly creature is not within five feet of you).
(Incidentally, in a low-level party with a Sharpshooter, there's a good chance that Helping the Sharpshooter land a shot against e.g. an orc will turn out to increase party effectiveness significantly more than making your own little weak shortsword attack for 5 points of damage on a hit. It's too bad that Help loses steam at higher levels.)
Final thought: my ruling on Help is that you get advantage, but you use the lower creature's bonus. E.g. two PCs with +4 and +5 on Survival respectively are trying to navigate the Underdark with a DC 10 Survival check. You can either roll at +5, roll at +4, roll both and just argue it out as to who to follow, or put your heads together and cooperate to get a +4 roll with advantage. Your familiar could try to Help you navigate but you're probably looking at +1 at advantage instead of your own +X so it's fairly pointless unless you're a real dunce.