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I had trouble making that decision as well. We decided to go with a four tiered cake with an extra sheet cake in the back. We have four flavors, one for each tier. For more flavor options, I would go with the cupcakes. However, as PP said, you could do one small cake for cutting and then cupcakes to go with it.
I agree with the PP. A 5-tiered wedding cake will be a beautiful focal point of your reception. So it really depends on what kind of wedding you want/are having--formal with a showstopping wedding cake, or more casual/laid back?
We are doing cupcakes with the small cake for cutting on top style...I had the cupcake idea before going to a bridal show but when my FMIL and my mom both fell in love with the cupcake idea at the show...I knew it was a winner...because FMIL is who I was worried about...lol but she proved me wrong...and then she surprised FI and me by wanting to pay for them...so hey..Im not complaning And since we not having any kids there except my lil sis(in wedding party) we dont have to worry about messes. So go with what you can afford and want..both work really well.