I have an update: a few weeks ago, I decided to hire a creative agency. I am too close to the problem, so an outsider's opinion is invaluable, and I'm an expert in illustration whereas others are experts at this very thing I need, branding. Sometimes I help with branding too, but it's not my main job, and in this case... it was not working. I also want to focus on my clients' needs during my time at work. I have been very excited about the new project, and tomorrow I am meeting with Brett Wilson at Creativibe to see the concepts.
I am so ready for an updated logo that's less "Victoria's Secret" and more "Shoemaker Medical."
Thanks for all your input along the way! I can't wait to show you the new look later this year.