Does Tandem Tactician allow helping two specific allies?

Question

The recently released UA includes the feat Tandem Tactition which reads:

Your presence in a scrap tends to elevate your comrades. You gain the following benefits:

• You can use the Help action as a bonus action.
• When you use the Help action to aid an ally in attacking a creature, increase the range of the Help action by 10 feet. Additionally, you can help two allies targeting the same creature within range when you use the Help action this way.

My understanding was that when the Help action was used to grant an ally advantage it was the next ally to attack the distracted enemy. The wording of Tandem Tactician clearly runs counter to this but my question is whether you can, using Tandem Tactician, choose the specific allies that get advantage from the help action (bonus action).

For a specific example:

Gerald is a fighter with Tandem Tactician. Gurt is a rogue, Wilhelmina is a wizard, and Sarsaparilla is a monk. They are all fighting Tiamat.

• Gerald attacks Tiamat and uses Help as a bonus action attempting to aid Gurt and Sarsaparilla in attacking Tiamat.
• Wilhelmina casts Firebolt to attack Tiamat
• Gurt fires her longbow to attack Tiamat
• Sarsaparilla kicks to attack Tiamat

Which characters have advantage on their first attacks assuming no other sources of advantage are applicable?

These questions relate to this issue with the Help action in general:
Do I choose the target or the ally for the Help action?
Can I Specify who the Help Action helps?

Answer 1

When you help allies with attack - you don't target allies. You target creature to distract - which is obvious from the answer to first question you've linked.

So, Geralt can't target allies to help them with attacks, he targets Tiamat and distracts her, giving his allies advantage on their attacks.

Normally, rules for using 'help' say that first attack of first ally to attack that enemy has advantage. But with this feat it works for two allies. But, rule for first attack stays.

So, in your example - Geralt's 'help' gives Wilhelmina and Gurt advantage on their first attacks. Even if Wilhelmina would use some multi-shot spell, like Scorching Ray - only first attack roll would have advantage. Same if Gurt somehow would have more than one attack - only first would have advantage.

Also, obviously, advantage doesn't trigger if something that doesn't need an attack roll is used. For example, if Wilhelmina would use a fireball spell that doesn't require attack roll - then benefit of 'help' would remain for first attacks of Gurt and Sarsaparilla.