Good raw bones for Stogie would be chicken wings, chicken thighs, chicken legs, turkey necks & pork ribs. I wouldn't feed anything much bigger/heavier than those to a little guy.
I would definitely work towards getting him used to a toothbrush. Start by letting him lick yummy-flavored dog toothpaste (I have chicken & mint flavors) from your finger, then from the brush, then have him "stay" and start gently brushing his teeth. Small dogs are sooo predisposed to dental issues & plaque build-up, it might prevent extractions & lots of dental cleanings in his future.