Is it permissible to offer Tahajjud prayer after Witr prayer?
It is permissible to offer voluntary prayer after Witr (An odd number prayer performed between Isha and Fajr) prayer. However, it is desirable that the night prayer be ended with Witr. Therefore, it is desirable for one, who thought that he was most probably going to wake up at night in order to offer Tahajjud, to offer Witr after it, but one, who fears that he might not wake up, should offer Witr before going to bed.
Is it permissible for the man to go out wearing shorts?
All Perfect Praise is due to Allah, The Lord of The Worlds
It is permissible so long as his Awrah (private part), which is between his navel and knee, is covered. However, the regular wear traditions and modesty are to be observed. And Allah Knows Best
Is performing Umrah an obligation for who is capable. Is he accountable for not performing it in this case?
Umrah is an obligation once in a lifetime for every Muslim. When physical and financial ability is present, it is preferable to perform Umrah, as well as Hajj. If one can afford to perform Umrah but not Hajj, then they should begin with Umrah, especially since Hajj nowadays is not accessible to everyone who wishes to perform it. In contrast, Umrah is more open and easier to undertake. And Allah knows best.
Does Istigfar (Asking Allah for forgiveness) between the first and the second part of Friday prayer`s sermon render the prayer invalid?
Talking during Friday prayer`s sermon is disliked, but there is no harm in offering Istigfar between the two parts of the sermon, and it doesn`t invalidate the prayer as it is actually from Sunnah. And Allah Knows Best.