Hi Christopher - I don't think it's possible currently, because when you boolean union 2 objects that don't touch, it's built into the booleans that such objects are automatically normalized and broken back out to be separate objects.

There is not currently any way set up such that 2 totally separate objects that do not touch each other can be combined together and select as if they were a single unit, that is going to require special support at a low level in the core selection code, it's not really something that can be scripted.

- Michael