So, I have had great success shipping my cookies with no problems. Has anyone ever shipped actual cookie bouquets with success?

Yes, I ship them. I weave small bubble wrap throughout the actual cookies, fill the bottom and sides of the box with larger bubblewrap, lay the bouquet inside and cover with more large bubblewrap. i pack it tight enough that it can't move at all when I shake the box. I just sent one to my mom in Idaho (I'm in Michigan) and she said it arrived in perfect shape.

Fantastic! Thanks!