For me helmets are pretty uncomfortable, I don't even like having to lace up shoes before skating so the fewer steps between me and skating the more likely I am to go and do it. I've lightly bumped my head once in a year of skating, if I was skating big bowls or ramps or bombing hills I would probably wear a helmet and kneepads. I think a lot of people don't even consider it though because the people they look up to generally don't wear them so why would they? There's a lot of thoughtless trend following in the skateboarding world and not many teachers going against it. Helmets and other protective gear will stop you getting hurt but they'll also remove some fear of injury which is what will teach you how to avoid getting hurt in the first place by falling correctly to avoid hitting your head/knees/elbows/wrists etc, no matter how much padding you wear you will get hurt eventually so it's good to learn to avoid those situations rather than just mitigate them. When you're doing higher risk activities this doesn't really apply though.

I just started skating a couple weeks ago and also have bad right ankle from an injury years ago. I’ve been skating a couple miles everyday and trying shuv its and Ollies. I can Ollie fairly well now. If you want to do jumping tricks, you might need to take it easy since your ankles will get pretty sore initially. I haven’t had any ankle pain; my feet tend to get the most sore.

I litch saw him recording 😭😭😭