What should a person who doubted having missed a pillar of prayer do?

All praise be to Allah, The Lord of The Worlds.                                                                                                                                                                              The prayer of one who doubts having missed one of its pillars is valid, and nothing is due on him/her since having a doubt after offering the act of worship doesn`t undermine its validity. And Allah 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.

What is the ruling on performing voluntary prayers during official working hours?

All perfect praise be to Allah, The Lord of The Worlds, and may His Peace and Blessings be upon our Prophet Muhammad and upon all of his family and companions

There is no harm if  there was break time during official working hours, but if not then it is impermissible. And Allah Knows Best.

Is prayer nullified by nose bleed?

 All praise be to Allah, The Lord of The Worlds.                                                                                                                                                                           Blood coming out of the nose, or a wound doesn`t nullify prayer regardless of its quantity. And Allah Knows Best.