I think you should slowly start to think about removing it because it will only become more and more his emotional crutch.
It is normal to be upset, and learning to deal and live with negative emotions is fundamental to mental health.
Bad things happen, from hitting your knee on the coffee table to have a "no" when you asked for extra chocolate.
You don't need to be brutal, but don't rush with the dummy, every time he is upset with something. He slowly needs to find way to console himself without it. Start forgetting it, or it is dirty or you need to buy a need one.
Every child is unique. Your DS is sensitive, which is very sweet but look ahead. You don't only teach to walk, talk, cross the road with the green man, but also teach how to deal with situation. Resilience and a strong self esteem come from failures (tower of blocs collapses) and building your emotional muscles.
Let him see you with your bad feeling. Being annoyed, upset , sad, and so on. Even bloody pissed at the delivery driver who cancelled last minute.
We shield our children from the bad and then despair when they can't deal with it as teenagers. Be honest in your day by day so that he learns that bad things are normal (bugger, I have no butter for my toast, that's annoying ) .
When to remove will be up to you. The more you wait however, the harder it will be.