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Doll Jogging Stroller | Pottery Barn Kids $89~ pricey, but adjusts to height and is well made so would last a long while.
I was obsessed with my cash register as a kid... back when stores still stuck price labels on things. Toy cash registers are great for teaching kids math in the concrete, using something everybody likes and should understand- money. You cannot go wrong, getting a kid a cash register, I think.