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.
What is the authenticity of the supplication: "O Allah, bring it upon us with blessings and faith, safety and Islam, and success in what You love and are pleased with. My Lord and your Lord is Allah"?
On the authority of Talhah Ibn Ubayd Allah (may Allah be pleased with him) who reported that the Prophet (PBUH) would say when he saw the crescent moon: "O Allah, let this moon appear over us with blessings and faith, safety and Islam. My Lord and your Lord is Allah."
This was narrated by Tirmidhi (Hadith no. 3451), who said: "It is a Hasan (good) Hadith."
And Allah The Almighty 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 to offer prayer at home, or should it be offered in the mosque?
All perfect praise be to Allah, The Lord of The Worlds. It isn`t preferable for the man to pray at home as praying in the mosque is twenty seven times more rewarding. Therefore, this should motivate him to offer prayers in the mosque. And Allah Knows Best.