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 a person who broke fasting in Ramadan because of being sick to pay a ransom?

If there is hope for him/her to be cured, then he would be required to make up for the missed fasting days when he/she recovers, and no ransom is due on him/her. If his/her disease is incurable, then he/she would be required to pay a ransom for each missed fasting day, which is (600) grams of wheat, or rice. And Allah Knows Best.

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 for a person who has to make up for missed fasts to fast six days of Shawwal (the month directly after Ramadan) before making up for the missed fasts?

Yes, it is permissible for him/her to do so, but it is better that they make up for missed fasts first. And Allah Knows Best.