Aiko is in slave mode when you have this menu. This is why the give item and other options disappeared. You need to cancel slave mode by clicking the doll mode choice then cancel the doll mode again to get her back to normal.
For your other feedbacks, namely the outfit bug, it must come from editing the save file only which can cause those strange occurrences but since it's not something you can achieve in a normal game, I won't debug it

For Rin saying she has no boyfriend despite you being her boyfriend, it's just random daily speech which does not check the boyfriend status. Boyfriend feature was added much later so some speech are indeed outdated but shouldn't be too problematic. I'll check it.