Re: Bottle before bed - almost 21 month old
We also transferred to a water sippy over night. Gradually offered less and less milk in the evenings and did fun reading/storytelling/songs - something to distract and be more fun.
For the teethbrushing - we do it while they are still strapped into booster seats after breakfast & dinner. They brush their own teeth as best they can (11mo old and 2.5yr old) then we follow up with a better brushing before unbuckling them. The 11mo old still sometimes screams while we do the followup clean. But, it's not up for debate, so we just plow on and wait for them to accept it.
A (usually) happy wife mama to my BOGO girls, DD1 July 2010 and DD2 Dec 2011.