I'm sorry, I lost track of all the issues you described, it's very difficult to understand what's going on without the project file.
The fact that the object is a member of a family should not be causing any issues with picking. I also have never experienced any bugs with using MoveTo and its On Arrived event, and I use them a lot.
Returning to your original question - if there are no containers, no hierarchies and no parent events which could've changed the picking scope, then there are really not many reasons left why the instance is not getting picked:
1. It's not created yet, or maybe have just been created in the same tick.
2. It's destroyed.
Like I said, try adding System Pick All as the first condition. Add instance counters (Obj.count and Obj.pickedCount) to Browser Log outputs, they should help with debugging these problems.