Re: EP and weaning...
After a year, a lot of moms either wean entirely or pump-wean and just nurse when they are together with their kids, so the fact that you're planning to continue pumping 4x per day even after your baby is a year is not something you should feel horrible about! I think you should feel very proud of yourself.
It seems like your big issue is that your baby loooves milk, and you don't want to deny that to her. As long as she will take whole cow's milk in addition to your milk, you won't be shortchanging her. If you run into a situation where your daycare provider refuses to offer breastmilk after age one, you can just let her have cow's milk at daycare and feed her your milk when you're at home. Though honestly I think the best thing to do would be to find a daycare that will feed your child in accordance to your wishes- I wouldn't want to send my kid to a daycare that said no to my milk!
I think the best way to transition from bottle to sippy cup is just to keep offering the sippy cup and try different types of sippy cup,and to give it time. Not all kids are ready to ditch the bottle at 12 months, and my guess is that a slow transition is going to be easiest for all involved.
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!"