Should he walk with his sister who makes a wanton display of her beauty (tabarruj)?

Firstly: 

You should advise your sister and explain to her the rulings on hijab and that it is haraam to make a wanton display of one’s beauty (tabarruj). May Allaah guide her and open her heart to the truth. 

It is important to be wise and patient, and to show love, mercy and compassion towards your sister when you speak to her. You should choose the most suitable ways and times for that. You could also use some books and tapes that will encourage her to wear hijab and will dispel her doubts.

 As for going out in the street with her when she is adorned, that is not permissible except in cases of necessity, because her going out like that is an evil and it is not permissible to help her in that, because Allaah says (interpretation of the meaning): 

“Help you one another in Al‑Birr and At‑Taqwa (virtue, righteousness and piety); but do not help one another in sin and transgression. And fear Allaah. Verily, Allaah is Severe in punishment”

[al-Maa’idah 5:2]

You should advise your parents and explain to them that it is haraam for a girl to go out in the street wearing adornment openly, and that they are responsible for that, as Allaah says (interpretation of the meaning): 

“O you who believe! Ward off yourselves and your families against a Fire (Hell) whose fuel is men and stones, over which are (appointed) angels stern (and) severe, who disobey not, (from executing) the Commands they receive from Allaah, but do that which they are commanded”

[al-Tahreem 66:6]

And the Prophet (peace and blessings of Allaah be upon him) said:

“Each of you is a shepherd and each of you is responsible for his flock. The ruler of the people is a shepherd and is responsible for his flock. A man is the shepherd of his household and is responsible for his flock. A woman is the shepherd of her husband’s house and children and is responsible for her flock. The servant is the shepherd of his master’s wealth and is responsible for it. And I think he said: The man is the shepherd of his father’s wealth and is responsible for his flock. Each of you is a shepherd and each of you is responsible for his flock.” 

Narrated by al-Bukhaari (893) and Muslim (1829). 

It is not honouring one’s parents to obey them with regard to tabarruj or going out with a woman who is showing her adornments openly, because there is no obedience to any created being if it involves disobedience towards the Creator. 

Secondly: 

There is no suggested annual schedule for reading, rather each person should work it out according to his work and free time, and the level of his comprehension, and other factors. What matters is that you should organize your time and have the desire to acquire and increase knowledge, as well as seeking the help of some Shaykhs to determine your priorities in reading, to solve problems and to explain difficult matters.  

If you cannot contact any of the shaykhs who are qualified to teach, then you can make use of tapes which explain the books of different disciplines, as well as seeking the help of one of your righteous brothers with whom you can study and organize regular appointments for getting together and studying which is one of the greatest means of attaining blessing.  

Thirdly: 

Reading books requires awareness, insight and the ability to make good choices, as well as methods that will help one to continue and succeed. With regard to this, we advise you to read a book called Kayfa Taqra’ Kitaaban (How to Read a Book), which you will find via this link (in Arabic):

http://audio.islamweb.net/audio/index.php?page=audioinfo&audioid=102290

We ask Allaah to help and guide us and you. 

And Allaah knows best.