All perfect praise be to Allaah, The Lord of the Worlds. I testify that there is none worthy of worship except Allaah, and that Muhammad is His slave and Messenger. We ask Allaah to exalt his mention as well as that of his family and all his companions.
The best way of wiping over the head when performing ablution is to do it as reported about the Prophet "…he wiped over his head with his hands, he started from the front of his head and wiped backward and then wiped from the back to the front until the reached the place where he started." [Al-Bukhari and Muslim]. Therefore, what is legislated when performing ablution is to wipe over the head and not wash it; wiping is a soft movement and does not require making the water reach the root of every hair as mentioned in the question.
What is legislated is to wet the hands with water and then wipe over the head starting from the front and then moving backward until the end of the hair from the back and then moving reversely to the front of one's head. Moreover, you should not consider your hair style as an obstacle when performing the obligation of wiping over the hair, and you should not consider it as a question of self confidence. The main important thing is faith, being steadfast on Allaah's Religion and having a good moral character.
For more benefit, please refer to Fatwa 84841.
Furthermore, you should avoid leading a luxurious life which will lead you to being attached to this world. The Prophet said: "Beware of relishing a luxurious life; the slaves of Allaah are not relishing a luxurious life." [Ahmad].
Moreover, exaggerating in your concern about your hair style is one of the characteristic of women and not that of men, so you should beware of imitating women, the disbelievers or dissolute people as the Prophet cursed men who imitate women and he also said: "He who imitates a people is one of them."
Finally, we would like to bring to your attention, that what we stated is pertaining to ablution. On the other hand, during a Ghusl (ritual bath) the hair must be washed thoroughly until water reaches the skin (the root of the hair).
Allaah Knows best.