Tim,concerning mid to high top shoes.....contact Chase. Nobody has more experience, knowledge or opinions about flatland shoes than Chase Gouin. He will guide you to the correct Nikes for your needs. If only somebody would make his signature shoe for him. It would be all anyone would wear.
if you really like support, try an ankle brace. its like a sock, just tight. i wore one for a while after i got off of my crutches.