Hi K.,
I had just read in a magizine about a couple of these issues you are talking about.
pacifier I read that as long you are using the pacifier in a controled way (as you are) and only at needed times and trying to wean from the pacifier you are fine.
Sippy cups on this issue it says that you should only put water in them and they should only be given the sippy cups with their meals at the table. Which in my opinion I see nothing wrong with what you are doing.
Dentist on this issue it says that when your child (no matter what age) gets their teeth they need to be seen by the dentist just to make sure everything is coming in ok.
In my opinion the pacifier is not something you can just take away and be done with in 1 day and every child is different with this issue. I say keep going you are doing great.
On the sippy cup issue I don't let my daughter carry her cup around all day with something in it at all times, but I let her have her cup after her meal that way she isn't getting filled up on what she has to drink.
I think you are doing an awesome job and keep it up. I would make an appointment for him to a dentist and at least get his teeth looked at and then go from there. Goodluck W. mom of 4