You are a great mama, and don't let anyone else make you feel inferior!
In regards to him waking during the night, that is COMPLETELY normal for anyone! I still wake up 1-3 times a night, and then fall asleep again, and I'm a grown woman! As long as he is sleeping a few hours at a time, I wouldn't sweat it. Some kids wake during the night and fuss and cry, others wake during the night, not making a peep and just go back to sleep without their parents ever realizing they woke up in the first place!
Do not stress about getting rid of the bottle immediately, he is still really young! I would just start putting milk in a cup at nap and bedtime and not look back. It will only be stressful for him for a short time, and the bigger deal you make of it, the bigger deal he will make of it. If you don't think that you will be able to do it that way, then start lowering the amount of milk he gets in his bottle at nap/bedtime, 1-2oz every other day, until he is down to 1 oz or so.
I had to do this with the little boy I had to nanny for, and it was much easier for me to get him off the bottle at naptime than it was for his mama at bedtime. (Very hard for her to let go, and the more upset she got, the more upset her son got)
You can do this J.!!!