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We booked our trip during free dining & my husband just found out that he'll have to leave a few days sooner than the rest of us. Can he still use Magical Express to get back to MCO since he's leaving on a different date? Would it mess up our free dining package if he did this?
Yes, he can do it. No, it won't mess you up.
If I were you, I'd keep it simple. Wait until you fly into MCO. When you check-in at the Disney Welcome Center (a.k.a. the DME counter), they will ask to confirm your return trip information. At that point, tell them what your husband plans to do, and they'll make the appropriate bus reservation for him.
If you want, you can also do this at your resort's front desk, instead. Just make sure you do it no later than about 1-2 days before he needs to leave.
It won't be any problem at all.