I use the Medela Pump In Style and I really like it! As far as bottles, we have used the Dr. Brown's with the preemie nipple (the nipple they come with is a size 1), at the recommendation of a lactation consultant. The slower flow is supposed to more similar to the flow from the breast. A girl from the La Leche League meetings I go to uses and highly recommends the breastflow bottle, which she said she got on Amazon. I haven't tried it.
A little tip we learned from a doctor we saw that specializes in feeding problems in infants... when using a bottle to simulate being on the breast, you can tip the bottle down so that no milk is in the nipple. The baby will suck, but not swallow (so they're not swallowing air), simulating the sucking a baby has to do before a let-down comes on. You can then "reward" the baby with the milk, like a let-down. If the baby seems to be gulping down milk too quickly, it's another good way to slow baby down without having to pull the bottle away. Might be a good thing to learn to teach your caregiver for when you are back at work.
Good luck pump and bottle shopping! I think there are many great options out there, you'll find what works best for you.