For anyone who might be interested or doing a similar function, my problem was in AddPickedItem, where the very first item of the dynamic list was set. ( pickedListStringP.stringListP=itemToAdd;) Because I was doing this by pointer, when the second item was added, the first list was freed, thus unintentionally freeing itemToAdd as well, which was a pointer to an item in another list. So two things were getting deallocated without my knowledge, and since the only time the program crashed was when I added more than one item to the list, I (mistakenly) assumed the problem was in the addition of items after #1.
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