Really like the idea of an english pub-style hanging sign. Also like the idea of a line-art style woman walking a dog.
I've decided to extend this first round so that I can take a bit of a new direction. Because I need the logo to work well for small print business cards and a website, I think I need to take this in a simpler direction. There are two possible directions for the logo that I'm looking for. Feel free to submit examples of one or both.
1) A vintage-style shape with filigree and a coonhound shape of dog in the center of it, with the name "The Heeling Hound" at the bottom, possibly inside or outside of the shape itself. You can leave out the "Pet Sitting and Dog Walking" wording for now. I think by focusing on just the dog, this would help it look better in a small size or at a distance, so that people can identify it easily, whereas the woman walking the dog is too detailed to fit within a sign shape.
2) A simple picture or silhouette type of drawing of a woman walking a dog in heel position on leash, either viewed from the front or the side, preferably with the woman and dog looking at one another or at least the dog looking up to the woman. The name "The Heeling Hound" could then appear at the top or bottom. If you can find a way to give this a vintage feel, that would be even better. I am open to a variety of ideas.
Also, the colors I'm going for are an earthy, moss green and brown with possible coppery orange elements as well.