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Your daughters can at any time perform an AOL(assumption of liability) and take over their own line without any penalty to you or and change to your plan as long as you still have more than 1 line on your account in order to keep your Family Plan. If you drop down to one line, you would automatically be switched to an Individual plan as you would only have one line. There are no penalties, though.
Once either/both of your daughters are out of contract, they can still do an AOL or can port their number to another provider with no penalties to you.
As to same-day renewal, of course all of the lines would need to be eligible for a discounted upgrade for the new contract dates to expire at the same time. If your daughters are not eligible for a discounted upgrade, they would not be signing a new contract if they were to get a new phone as they would receive no discount off the retail price of the phone.
