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.
I took a housing loan from the bank for a 20-year period. Four years have passed, and I recently learned that this loan is usurious. I wish to perform Umrah. Am I permitted to perform it? If not, what should I do?
You are permitted to perform Umrah. Strive to repay the debt in hopes of reducing the amount of usurious interest. Allah Says (What means): "And there are others who have acknowledged their sins. They had mixed a righteous deed with another that was bad. Perhaps Allah will turn to them in forgiveness. Indeed, Allah is Forgiving and Merciful." [At-Tawbah/102]. And Allah Knows Best.
Is wearing a cap permissible for boys, or girls?
All Perfect Praise is due to Allah, The Lord of The Worlds.
In principle, anything is permissible sol long as there is no Sharia evidence prohibiting it, thus wearing the cap by boys is permissible as long as it isn`t done in imitation of the disbelievers. Moreover, a Muslim woman should avoid all that which attracts the attention of men because whatever leads to the forbidden is forbidden. And Allah Knows Best.
Is it incumbent on the fiancée to obey her fiancé?
When the woman settles in her husband`s house, it is incumbent on him to provide for her and it is incumbent on her to obey him. Before that, and if the marriage contract had been concluded, then she is lawfully his wife and thus she should abide by custom in treating him, but if the marriage contract hadn`t been concluded, then she should treat him as a non-Mahram (Marriageable).