Hi A., I nursed through the beginning of my second pregnancy throughout the first trimester. Then, as I had been warned, my milk supply dove, and my son weaned himself because the taste and flow had changed. Just as well since I too had high risk pregnancies (fraught with pneumonia, severe asthma/sinusitis/allergies, insulin dependent gestational diabetes, as a start). My midwife encouraged me to stop nursing sooner, to protect my own immune system and therefore the fetus as well. (My son was 8 months at the end of my first trimester).
We weaned my son to a sippy cup and milk at the same time, the week before his 1st birthday. He was really mad! Here's what we did: first we watered down the milk and tried warming - didn't really help. So we did a gradual changeover: For a week, we got rid of bottles during the day, sippy cups only, with milk in them. He basically didn't drink anything except the water offered between meals, for 4 days. He still had wet diapers though so we stuck with it, and after the 4 days, he started drinking the milk just fine. The next week, we got rid of the morning bottle, and the following week we had planned to get rid of the night time bottle but he had lost interest at that point. It's been sippy cups ever since. We HAD to get rid of the bottle because his sister would be arriving in less than 6 weeks and we didn't want to be dealing with jealousy about bottles for those few times we would have to use them with pumped milk. Since you've barely used the bottle up to this point, I would recommend skipping them altogether. Hopefully my experience helps!
My son (who is now 22 months) will not drink any yogurt smoothies, flavored milks, even juice for the most part. Some of these things may work for you though. I have a relative that mixed milk and oj and her kids love it. (Yuck, they call it "milky-juicy!") I have heard that we should be starting to introduce whole milk in really small amounts at the 9 month mark, to help with the transition. I may research more abut this and try with my daughter (who's 8.5 months now), but I haven't decided yet.
Congratulations on your pregnancy and good luck!