I worked in a grocery store bakery and made these a lot. I would just put a dot of icing on the bottom of the cupcake wrapper, place it on the board and ice the top as I would a normal cake. Icing does get into the center, but does not "fall" through....unless it is very thin, of course.
After attaching your cupcakes to your board (using a small dab of buttercream) frost the cupcakes as one, not individually. If you have the larger Icer tip (#789), it works really easily. Otherwise, just ice as normal. If you are using a crusting buttercream, you can use the Viva paper towel technique on this. Your icing will NOT fall into the gaps between your cupcakes. Good luck and be sure to post pics! 
Thanks madicakes and crisseyann for the advice. I will post my pics up. Its for a cake made of 100 cupcakes and it will be of the NFL Raiders. I recently tried really quick with 24 cupcakes and asked my family to critic me and so they did. I put buttercream with tip #789 and on all of them. Secondly I smoothed out the frosting but then I put more buttercream and it was to much. But tomorrow I will try another 24 cupcake try out I'll post pics on that one ok. Thanks ya'll.
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