With regard to your writing about covering your hair - there is absolutely no question regarding this matter: Since G-d clearly said that for the benefit of the wife, her husband and their children the hair should not be revealed, surely it is so. Thus it is impossible that by keeping G-d's commandments the head should hurt, etc.

For example, when you write that wearing a sheitel makes your head hurt, it is possible that:

1. This is a falsehood of the Evil Inclination who does not want Mitzvos to be performed and does not want Jews to be showered with blessings.

2. If indeed it is true - then this proves that you should cut your hair that it be short. Then it surely won't hurt when you wear a sheitel.

Excerpt from a letter of the Rebbe, Likkutei Sichos, Vol. XXXIII, p. 264