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You don't need to return to Masjid Shajarah from Makkah, but just need to go to Tan'eem which is very near to Makkah for Ihraam of another Umra. Tan'eem is known to all taxi drivers in Makkah.

Wassalam.

No. It is not permissible to enter Makkah and it’s surrounding area which is called Haram of Makkah with out Ehraam.

Wassalam.

Bismihi ta'ala

According to our jurists, there are about twenty five prohibited acts during Ihram, and one of them is tadhleel, or being under a shade for a male during the day while travelling. This means a male cannot be directly under any shelter during the day time when travelling from the Miqat to Meccah al-Mukarramah, but then inside Meccah, he can. 

In looking into the wisdom behind this, I have not come accross a reliable reference that explains this, but it seems that one possibility could be that it is a sign of humility. Instead of the person travelling with extravagence and comfort, he commences his spiritual journey of humbling himself by being under the sky. 

And Allah knows best.

Umrah is a very important worship which can be performed during any month in the year, not like Hajj which has its special time in the month of Thil Hijjah. Umrah Mofradah includes Tawaaf around the Ka'ba and Sa'ee between Safa and Marwah which was performed by all the Prophets and Unfallible Imams.

Umrah Mofradah has been mentioned in authentic Hadeeths and reward of it is the forgiveness of all the sins.

'Wassalam.