A. If moving him to his own bed is difficult because you are not ready and you both sleep well together, then that really isn't something you need to change. In fact, many experts actually advocate a family bed and so you shouldn't feel guilty about letting him sleep with you.
It is a different matter if you want him to move to his own and are finding it difficult because he simply isn't ready. In that case, you might just keep a strict bedtime routine and end it with his going to sleep in a crib in his own room. You might have a few rough nights, but he should quickly get used to sleeping in his bed. If you have to, you could sit next to his crib until he falls asleep or find other ways to comfort him. You might also consider a sleep parenting book if you need extra help.
As far as the bottle is concerned, that is a problem if he is falling asleep with it, since it puts him at risk of developing cavities. If you give it to him after his bath and then take the time to clean his teeth, then it is not that big a deal if he still takes a bottle. Switching over to water and then either moving to a sippie cup or gradually putting less in the bottle might be good ways to get him off his bottles.
