Is it permissible to pay the expiation of an oath to a charitable party as it feeds the poor and needy such as Tkiyet Um Ali?
There is no harm on authorizing someone to handle the expiation of another to the poor and needy, since Shafiee's jurists stated that authorizing someone for the purpose of distributing Zakah, expiation and vow is permissible as stated in [Mughni Al-Muhtajj,vol.3/pp.237]. At last, the intention of the person who intends to authorize someone else suffices in this regard. And Allah Knows Best.
Is it permissible to listen to chants praising the Prophet if accompanied by musical instruments?
If singing, or chanting in praise of the Prophet was accompanied by a forbidden musical instrument, then it is forbidden.
Is it incumbent on a family to provide for its old handicapped son and take care of him?
The family and relatives - e.g. brothers - of such a person are obliged to spend on him and take care of him if he didn`t have money of his own.
My headcloth is causing me a terrible headache and severe shortsightedness. Is it permissible for me to take it off?
All perfect praise be to Allah, the Lord of the worlds. I testify that there is none worthy of worship except Allah and that Muhammad, sallallahu ‘alayhi wa sallam, is His slave and Messenger.
If the headcloth Khimar is harmful, it is sufficient to wear the Niqab (face-veil). However, with the passage of time you will get used to the Khimar and these symptoms will go away. And Allah The Almighty Knows Best.