To freeze cupcakes and cakes or not?

Since the beginning of my baking days,
I have always been very skeptical of freezing cakes, breads, cupcakes, cookies, and ect

I am worried with the freezing that it will suck the moisture out as it thaws out

I have read a lot on a few blogs that they say they freeze up nice
but only last for a couple of months

I have a few big events to bake for coming up in the near future
1- for 300 cupcakes or 25 dozen in Gering
2- 200 cupcakes for a wedding in Denver

For the wedding in Denver, I am considering freezing the cupcakes the night before so they stay good for the ride down
I am going to frost them once I get to Denver for the wedding

Then I thought I would just make all the cupcakes the night before,
place them in sealed boxes and then drive the 3 hours to denver.

Any advice on freezing?

Begin discussion :)