dnd 5e – Do two simultaneous Orientation releases increase the probability of a better result?

Working together it's better than trying to stack address

Having the PC try the task adds 1d4 to a roll with beats of advantage when trying to stack 1d4, that you can not do anyway due to the magic effect combination rule that you have already quoted.

I have done it in several situations in which my cleric throws address in our barbarian, and then another of the players provides help that It gives the barbaric advantage over survival. roll (in search of food in an adventure in nature) or in the track of athletics (in a case in which we wanted to make sure we had thrown a door).

The average bonus of the guide is 2.5 (pulling a 1d4), while the expected benefit of having an advantage is between +3 and +5, depending on the difficulty of the task. (See this question and the answer for a thorough treatment of what the advantage benefit is when 2d20 is released). What you might expect as a benefit is the +1d4 guide and an additional +4 (+/- 1) depending on the DC of the task.

Working together
The character leading the effort, or the one with the highest skill modifier, can Make a skill test with advantage., reflecting the help provided by the other characters. (Basic rules, page 62, italics mine)

Have Bob help Charlie after Alice's guidance. Charlie 1d4, and rolls with advantage.

Warning: unless both characters have competition with the thieves tools, this will not work in the selection of locks.

We have also combined advantage and guidance to avoid getting lost in the jungles / forests of Chult (Tomb of annihilation Adventure published) where before doing my Wisdom check (Survival ~ Navigation), the cast of the cleric address. I already have an advantage because my favorite land is the forest. (This is how the DM governs it.) I can see how another DM would require a different approach (Ranger helps the hired guide, the cleric guide the guide, unless the ranger's PC is originally from Cult)).