Will repeated adrenal crisis weaken the adrenal gland?

No: People have an "adrenal crisis" only when the adrenal is already very weakened or absent. The crisis can be dangerous, but will not affect the gland itself.

Adrenal crisis: It is a weakened or damaged adrenal gland that causes the adrenal crisis, so the crisis itself usually won't further damage the gland. The exception is if you develop severe hypotension which can cause ischemia and damage to the gland (as well as other organs). That would really be a life threatening crisis though.