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I usually packed a whole unpeeled banana or avocado in DS lunch bag. Daycare is awesome and would mash or cut up the banana or avocado before they gave it to him. For other things I would just bring regular tupperware tubs of diced fruit, veggies or meat. I probably packed more than he could eat in a day but he's such a good eater at school. He had 2 snacks (mid morning, and mid afternoon) and 1 meal (lunch) a day at daycare. The snacks were usually same thing as the lunch but not as much food.

Once your son starts eating at daycare then you'll have a better idea how much to pack. If it's too much you can always bring it home for his dinner.

I would continue to send the same amount of milk until he shows signs of not wanting so much anymore. When he eats more solids he'll have problems finish a bottle or refusing it and you can reduce the amount or eliminate a bottle. DS went from 3 bottles to 2 at daycare within a couple of months of starting solids.

I buy my purees so I just send a container. When we send oatmeal, I send milk in a bowl and let them mix it up so it is fresh. Check with your day care, we have to have her name and date on the container. We also just send "lunch" right now.