What is the virtue of performing ‘Umrah in Ramadan?
Ibn ‘Abbas narrated: "When the Prophet ﷺ returned from his Hajj, he said to Umm Sinan Al-Ansariyyah: ‘What prevented you from performing Hajj?’ She replied: ‘Abu So-and-so (referring to her husband) had two camels—he performed Hajj on one of them, and the other was used to irrigate our land.’ The Prophet ﷺ then said: ‘Performing ‘Umrah in Ramadan is equivalent to Hajj with me.’" [Narrated by Al-Bukhari]
The Prophet ﷺ also said: "An ‘Umrah in Ramadan is equivalent to a Hajj." [Narrated by Al-Tirmidhi]
For those who miss the opportunity to perform ‘Umrah in Ramadan, there are many other ways to earn great rewards. One of them is praying Fajr in congregation, then remaining in the mosque remembering Allah until sunrise, and praying two rak‘ahs.
The Prophet ﷺ said: "Whoever prays Fajr in congregation, then sits remembering Allah until the sun rises, and then prays two rak‘ahs, will receive the reward of a complete Hajj and ‘Umrah—complete, complete, complete." [Narrated by Al-Tirmidhi]
Which is better for a traveler: fasting or breaking the fast?
Fasting is better, unless it causes hardship—in that case, breaking the fast is better.
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.
Is an elderly or chronically ill person required to pay additional fidyah if they delay it beyond the first year?
An elderly person or someone permanently unable to fast must pay fidyah by feeding one needy person for each missed day.
However, if they delay paying fidyah beyond the first year, no additional fidyah is required.
This differs from someone who delays making up missed Ramadan fasts (qada) without a valid excuse until the next Ramadan begins—such a person is required to pay an additional fidyah for the delay.