You did not mention what is the end point of differentiation. If you are differentiating to bone cells or lipid cells ( osteogenesis or adipogenesis) or on monolayer, there will not be difference. If you are differentiating into 3 dimentional cartilage or other tissue, than there will be a difference between dishes, I will use 24 well in that case first and than move to bigger wells. It depends on all that,