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.

Is it permissible for a man to marry up to four wives (polygamy in Islam) for pleasure although he can`t afford that?

It is desirable for the man to have one wife if there was no need for him to have more, if he can't afford marriage forthcoming expenses.

Is wearing a cap permissible for boys, or girls?

All Perfect Praise is due to Allah, The Lord of The Worlds.

In principle, anything is permissible sol long as there is no Sharia evidence prohibiting it, thus wearing the cap by boys is permissible as long as it isn`t done in imitation of the disbelievers. Moreover, a Muslim woman should avoid all that which attracts the attention of men because whatever leads to the forbidden is forbidden. And Allah Knows Best.

What is the ruling on the chatting between a young man and his girlfriend?

Private chatting between the two sexes entails religious violations, and leads to prohibited attachment.