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From what you all have done, I think I'll go ahead and start giving him whole milk at lunch time to start the transition. He's already using a sippy cup for water and sometimes formula, so the cup won't be the problem. I just hope he likes the milk. He loves familiarity and with food he's extremely particular. As far as weaning him from the bottle, I don't think the night time one will be the problem, but the one he wakes up for at 5am is my big concern. I'm still working out my plan for how to wean him off of that bottle. If you have any ideas on that, feel free to let me know!
Thanks for the input!
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