Brittany, your concerns are exactly why I only have one dog. I'm an empty nester and it's much easier to bring one dog with me when I visit my family. It's also much easier to take one dog to run errands. Lady is very special to me and I would never want to have to divide the love and attention either.
Lady also has tons of health issues and I am so glad I never got another dog. Those vet bills can really rack up as a dog ages anyway, but I can't imagine doubling them.