Out of four kids, we've had one who took a soother as a baby, one who never took one, and two who were totally, completely addicted to it. By the time Caleb entered junior kindergarten he was easy going enough that when daytime naps were eliminated, so was the soother. Up until that point I never fought it, because without the soother he didn't nap; with the soother he would sleep 3 hours in the afternoon. My plan had been the same with Benjamin.
However, Benjamin gave up naps about three weeks before school began. Sleep deprived from night nursing Juliette, I left him with the soother because every day I hoped he might nap again. Now I find myself one week into school for him, and he still uses the soother at night.
I tried a few different things. I tried telling him that as a big boy he didn't need it. I tried telling him we would throw them all away and go buy a special treat. I tried telling him we could gift them to a new baby (who, Ben insisted, would trade them for chocolate.) I had that last one all worked out. Benjamin chose a little baby, his friend's baby brother, and I bought little chocolate bars to trade, one for each soother (yes, we have a stash!) But no matter much we talked about it and agreed upon it during the day, come nighttime Benjamin was too emotional to remember the rational conversation from earlier in the day.
So I've let it go, for now. Sometimes using major life events are a great way to transition. Sometimes it's too much all at once. Benjamin is tired come dinner time, and although he doesn't nap after lunch, he still can't quite make it (pleasantly) all the way to bedtime. I plan to give him another month or so and see how he's doing, then maybe try again. Or not. The thing you realize this far into parenting is not to sweat the small stuff. And this, this is small stuff :)