Is it true that weaning definitely will have to go through engorgement? Does weaning (due multiple medical advices from few different Doctors) has to be so emotional and stressful ? What are the ways to make it easier..

I think weaning is about preparation. Both you and your baby should be prepared for this event. Try by decreasing the frequency of breastfeeding, distract him with something more interesting when he asks more. By the time, he will learn that breastfeeding is not for him anymore :)