Shane, my biggest concern was that there was a HUGE disconnect between what I wanted to be done and what was actually performed (mostly due to the fact that my designer outsourced most of the 'design' part to the Philippines, so there was a big gap in the translation - I didn't know this until it was too late).
There are a number of talented designers out there, be diligent and thorough as you vet out your web developer/designer and you will be fine. Best of luck.