Hard to say what exactly is going on with Tucker... I had a couple of thoughts.
Sounds like Tucker could be doing a good job of training you.
You are not alone, we are very well trained by our dog too! Chesapeake "talks" to us every night to get a treat. Once she has it she's content. Tucker could just be in the habit of wanting a your attention at that time. You could try putting his leash on a bit before he starts asking for it. Then it's under your control instead of you giving in to his demands.
Or there could be something triggering his reaction... perhaps a neighbor coming home from work that he hears?
Three things you can try....
~ The above thing with the leash. Catching him BEFORE he starts barking and putting his leash on or to bed.
~ Ignore him when he's being demanding and praise/reward when he's quiet.
~ Distract him or give him a command to do instead of barking.
How Chesapeake "talks" doesn't bother us... it's very cute not really a bark. But if Tuckers action is obnoxious, to you, then taking the time to break the habit is time well spent. Just be consistent... don't allow it sometimes but get angry others.