Does wiping over one's socks during ablution permissible?

If the socks were thick,  then wiping over them during ablution is permissible so long as wiping conditions are observed. And Allah Knows Best.

Is the Saum (Fasting) of someone who ate and drank forgetfully while offering fasting of oath expiation invalidated?

Whosoever eats, or drinks forgetfully is exempted by Allah; therefore, he/she shouldn`t break their fast whether it was obligatory, non-obligatory, or expiatory. And Allah Knows Best.

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 it permissible for a sick person to pray while sitting on a chair?

All perfect praise be to Allah, The Lord of the Worlds                                                                                                                                                                        It is permissible for a sick person, who is unable to stand up, to offer prayer while sitting on a chair. If he/she was unable to prostrate while on the chair, the he/she should pray while sitting on the ground, but if he/she was neither able to bow (Roku),nor to prostrate, then he can do them while sitting on the chair. And Allah Knows Best.