If I'm skating mini or just transition in general, I can get away with mids, but for street I have to ride highs. I've had to wear braces on both ankles (while skating) for years... they're both permanently egg'd and shot to shit. If I skate lows with braces (basically the S One's but Ace and Mueller makes some good rigid braces too) I can still roll it.
One weird thing though, since I skate with my feet pretty much immobile (no flick), when I do kickflip variants I have to sort of pop, then quickly step down in the air for the flip. I also noticed that in some cases weird contortions from bailing that might damage my ankles travel up... I'm pretty sure that's why I tore my meniscus a while back (dorking on a little portable rail). I think I would have just rolled my ankle again, but since the brace wouldn't budge, the weight I was putting down settled on the next best joint.
Bah, I fucking hate ankles.