Bedtime help

Tina

Dealing with ear infections, colds, and pneumonia all year so we unwittingly created a sleep issue. We started putting a pillow in her pack and play to prop her head up, so now she can't fall asleep without one. Also, I've been working two jobs all summer so I've been so tired at night when she wakes up I'll just prop her on a pillow in my bed with a bottle and we all fall asleep that way. Now she won't go back in her pack n play after her mid-night bottle. I'd like to get her in her own room in a crib. Am I just going to have to let her cry it out? I feel like I've ruined her! Are there sleep training resources that have helped any of you?