Hi Laura sounds like we are in a same boat. My lo is also 14m old and wakes all night long, same as your, most night she sleeps fine till 10/11 and then up up up all night long. We have a prop issue unfortunately and I think that might be the case with you and the bottles.
It sounds like your son is also getting ready for 2-1 transition.
The first nap is early. He needs it early because he is tiered from waking at night. Even if he insist, I`d try and push it 10-15 minutes at a time. Your goal would be moving it till 11 for start then maybe even 12.
I`d also stop the milk at night. He is eating well and he is old enough to go trough the night with out it. You can try and cutting the oz of milk slowly. What I did was drop an oz every 4 nights for the night feed. Or diluting the formula (cutting the number of scoops of formula).
About the dummy, what I do is 4 in the crib,(have read someone putting 8 ) some are what I call night dummies, they have some florescent part that glows and its easy to find.
HTH
Dache