Oh my goodness with my excitement thinking about getting the new puppy, I didn't think about the ordeal of walking them both. I love retractable leashes because it gives Kirby the freedom she likes. Also I can reel her back in when needed. With a new puppy do you have to start them with a regular leash? I like the idea of walking them with separate hands. I will be looking like a crazy lady too! I can't imagine 3 or more. At least with two you can scoop them up if necessary. I always carry a long stick when walking. I'll have to figure out how to walk like a crazy lady and carry my big stick .