How are gaps filled during congregational prayer?

A praying person is allowed to take two steps in order to fill the gap in the row ahead. If the distance was long and requires much movement, then it is impermissible for one to move to fill it because much consecutive movement (three movements) during prayer invalidates it.

Is it permissible to say: "O Allah, by the status of the saints and the righteous, and our master Muhammad, peace be upon him, grant us the ability to reach Ramadan"?

What is mentiond by the righteous predecessors that they used to say: "O Allah bless us in Shaba'an and Rajab and give us the ability to reach Ramadan." [Shoa'ab Al-Iman/vol.3/pp.375]. And Allah Knows Best. 

If a father stops his daughter from getting married, is it permissible for her to conclude the marriage contract herself?

It is permissible for the father to stop his daughter from getting married if there was a lawful reason for that, and she isn`t allowed to conclude the marriage contract without her guardian. However, if her father denied her right in getting married for an unlawful reason, then she should go to court.

Is it permissible for the man to go out wearing shorts?

All Perfect Praise is due to Allah, The Lord of The Worlds

It is permissible so long as his Awrah (private part), which is between his navel and knee, is covered. However, the regular wear traditions and modesty are to be observed. And Allah Knows Best