Oh Ryn, my DS is EXACTLY the same. Always wakes after first sleep cycle when put to bed for the night. I do the resettle in the dark, without picking up or speaking so that it doesn't matter who does it. I went out and left him with my mum the other night and she went in, replaced dummy, little pat and back to sleep without really noticing who it was. Would he settle for someone else if they did exactly the same as you would? I find that resettle quite quick as they kind of know it's the night and sleep for several hours after it so don't wake fully IYKWIM.