What is the ruling on someone who vowed to fast for two consecutive months, but failed to do so?

He is obliged to fulfill his vow by fasting for two consecutive months, but if he fails to do so then, it remains a debt on him until he either fulfills his vow, or dies. In case of his death, his guardian is supposed to fast on his behalf, or donate food from his estate in return for fasting, but if the guardian fails to do so then, it is all in the Hands of Allah.

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

Is it permissible to delay menses by using medication in order to fast Ramadhaan?

It is permissible for a woman to use medication in order to delay her menses so that it becomes eligible for fasting Ramadhaan, but it is better that she doesn`t do so, and taking the medication is prohibited if she, or her doctors knew that it involves risk on her health. And Allah Knows Best.

What is the difference between Tahajjud prayer and night prayer, and do they have a particular Witr prayer other than that of Isha (evening prayer)?

Tahajjud and Qiyam-Al-Lail (night prayer) are two words for the same meaning which is offering voluntary prayer at night after sunset, but before dawn break. However, Tahajjud is offered after waking up; whereas, Qiyam-Al-Lail is permissible before sleeping, or after it. Therefore, every Tahajjud is a Qiyam, but not every Qiyam is a Tahajjud. Moreover, there is no specified Witr for both of them, but Witr after Isha is by itself the Witr of Qiyam, and it is a Sunnah to postpone it until after Qiyam if the worshiper thought that he was most probably going to wake up in order to offer it, but if he wasn`t sure of waking up, then he is at liberty to offer it before going to bed as was reported in the Prophet`s Hadith.