Some day they will meet....
Chris - I have never had a problem with dogs and cats especially in the house. Outside, where chase can ensue is another story. I would expose them as much as your heart can handle. The faster, the calmer, the better. I would keep Bob on a leash while Ebby does her wandering....and treats, lots of treats for good behavior would be good for Bob. I bet Bob will be fine with Ebby. Sometimes dogs and cats can be the best of friends. I won't worry too much about this arrangement.
Keep us posted.
:)