Well, I'll tell you what I'm doing.
I have to return to teaching in October, so I decided to start getting Christian used to a bottle early. I'll be able to feed him before work and then again at 4:30 or so after work, so that means he'll have 3 bottles while I'm gone. So i started this week giving him the bottle for the first feeding I'll be away which was at 9:00 am. I'll do that for 2 weeks, then add the second feeding as a bottle around 12:00, do that for 2 weeks, then add the third around 3:00. That way, he adjusts, my milk supply adjusts and he doesn't go through changes of me being away, him being with a stranger and not being able to nurse, all at the same time. i'm just trying to ease him into it. Make sense?
Hope that helps give you some ideas