Alignment Hierarchy and Auto Align to Artboard
Alignment should work (Like most other design software) where there is a Parent/Child hierarchical relationship. Currently only "Align to left, and top" behave this way. Align to Center causes the two objects to meet halfway between their artboard positions. This is has been a major issue for years.
- Touch Parent object (anchored in artboard position)
- Holding Shift, Touch Child object
- Selection alignment task
- Child moves to parent
In addition, the selection of "Align to Artboard" should be an automatic default state for single or grouped objects. There is no need to have a selection for "Align to Artboard".
As per the comment, this can be done by clicking one of the selected objects to define it a key, to make all other object in the selection to align to this key.
Other apps rely on order of selection, and this is something users request to able to toggle here: http://illustrator.uservoice.com/forums/333657/suggestions/39711583
As for the Align to Artboard switch — it is useful when you have a selection of objects and want to align all of them to an artboard. In these cases the default mode Illustrator enables is Align to Selection, and you have to toggle it manually.
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Micah, do you know about key objects?
The thing you want to achieve is done with these.
You can read about them here:
https://helpx.adobe.com/illustrator/using/moving-aligning-distributing-objects.html
But in short, you need to have just one more step between your 2 and 3 — click (not sure why you said 'touch') the 'parent' object again to set it as a key object (it will become highlighted with a thicker edge).'Parent' and 'child' in Illustrator mean other things, that’s why perhaps you didn’t find the proper way to align objects to each other.
Doe this help, or did you find it by yourself (2018 was 4 years ago)?