Should a person feel pleased, or have a virtuous vision after offering Istikhara (guidance prayer) in order to do what he/she had offered it for?
The result of the Istikhaarah is not necessarily that a person sees something (in his dream), or feels pleased, but the most important result of the Istikhaarah is whether a person is enabled to do a given matter or not.
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.
What should one who made an intention, at night, to make up for a missed fasting day, but broke his fast on the next day?
One who started making up a missed fasting day, then broke his/her fast without a legitimate reason is considered sinful, and is only obliged to make up for the missed fasting days. And Allah Knows Best.
Is it permissible to fast on behalf of the dead who died owing missed fast to make up?
His relative should fast on his behalf, and it is permissible for the guardians to give permission to non-relatives of the dead to fast on his behalf as well. And Allah Knows Best.