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.
"If the fidyah becomes obligatory upon a pregnant or nursing woman because she broke her fast out of fear for her child, is it obligatory from her own wealth, or from her husband's wealth?"
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
The fidyah (ransom/compensation payment for breaking the fast) is obligatory from the wife's own wealth, and is not obligatory upon the husband unless he voluntarily chooses to pay it on her behalf.
It is stated in Mughnī al-Muḥtāj (Vol.2/P.174): "If the two [the pregnant woman and the nursing mother] fear for the child alone — such as a pregnant woman fearing miscarriage, or a nursing mother fearing that her milk supply would decrease, thereby endangering the child — then both the qaḍā' (making up the missed fast) and the fidyah become obligatory upon them, to be paid from their own wealth." And Allah, the Exalted, knows best.
Is it permissible for a woman to wear underwear while performing Umrah?
Yes, it is permissible for a woman to wear underwear while performing Umrah. This is because she should keep her regular clothes that cover all her body while being in a state of Ihram (ritual consecration) for Hajj, or Umrah. However, she should uncover her face and hands, but it is permissible for her to let her head-covering garment drape from her head down over her face when non-Mahram (i.e., marriageable) men pass by her. And Allah Knows Best.
If someone delays making up fasts for a year, can they give fidyah before performing qada?
Yes, it is permissible to give fidyah before making up the missed fasts (qada), because each is an independent obligation, and there is no required order between them.