What is the ruling on istibra' and how is it performed?

Istibra' (cleansing from urine) is recommended. It is for a person to ensure that nothing remains of urine in its passage before performing istinja'. Its method is: to clear the throat (or cough slightly), shake the penis (meaning to pass fingers along it to expel any remaining urine if needed), and walk a few steps to the extent that one thinks nothing of urine remains if walking is needed. Each person knows his own nature best. The preferred opinion is that this differs among people. The objective is for one to think that nothing remains in the urinary passage that he fears will exit later. And Allah the Almighty knows best.

Is it permissible for an elderly person, a pregnant woman, or someone with a chronic illness to pay fidyah before Ramadan begins?

What is the ruling on a person in a state of major impurity (junub) walking or eating before performing the ritual bath?

It is from the Sunnah for a Muslim to hasten to perform the ritual bath for major impurity. However, if he delays it, he does not sin provided he does not miss the prayer. It is permissible for the junub to walk, eat, drink, and sleep. It is recommended for him to perform ablution before these actions to reduce the state of impurity, although the best is for him to perform the ritual bath. And Allah the Almighty knows best.

If someone regularly fasts the six days of Shawwal, are they obligated to fast them every year?

A person is not obligated to fast the six days of Shawwal every year, even if they have made it a habit. However, someone who regularly performs a good deed should not abandon it as long as they are able.