Re: Breastfeeding and sleeping
Your doc's advice stinks, not to put too fine a point on it. This link explains why breastfeeding isn't linked to tooth decay: http://kellymom.com/bf/older-baby/tooth-decay.html. And WRT sleep, there are plenty of good reasons why babies wake at night. Teething is probably the biggest one. But a baby's need for mama and papa, the need for a diaper change, and yes, even hunger can keep babies waking at night!
It sounds like you've actually gotten your nighttime situation into fairly good order, and your real problem is that your baby doesn't always go right back to sleep. Yes? What if you just nursed him to sleep at those nighttime wake-ups? In my experience, it's getting the baby to sleep the first time that's the most important in terms of setting the sleep pattern for the night. After that, you do what works.
Coolest thing my big girl said recently: "How can you tell the world is moving when you are standing on it?"
Coolest thing my little girl sang recently: "I love dat one-two pupples!"