If your HR department approves you to go on medical leave, can your immediate supervisor "grill" you about your condition?

In addition, while you are on medical leave, can your supervisor text you and tell you complete tasks that constitute as "work"?

I moved this to it's own thread.

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If your HR department approves you to go on medical leave, can your immediate supervisor "grill" you about your condition?

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Yes. Your supervisor has an interest in knowing why you aren't at your job.

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In addition, while you are on medical leave, can your supervisor text you and tell you complete tasks that constitute as "work"?

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Absolutely.

What if your condition has left you physically incapable of being able to perform them? i.e.. Asking a stroke victim with nerve damage to do some typing

Then report it to your HR department. Its up to HR to deal with it.

Yes he can ask about condition, you do not have to tell him, unless your company policy requires it

If you had a stroke, obviously the supervisor will know about it.

But they can not require you to do work while off on leave, but can keep you updated