My first run with the stroller and both dogs may not seem like a big deal or may seem crazy, either way for me this was a big accomplishment that required gradual build up. I started with just the stroller then one dog then both dogs. At our 4 month appointment the pediatrician gave the go ahead to begin stroller running, I wanted to stick to paved smooth surfaces like a trail to keep the bumping and bouncing to a minimum but on our first weekday run I felt venerable with just me and the stroller. So the next run I brought our lab along for protection and to get him out of the house as he has the most cooped up energy, leaving our Blue Heeler behind not sure I could control or manage all 3. I shouldn't care so much about the dogs "feelings" but I hate to leave either one behind, they get so excited when I lace up my shoes.
The most difficult part of this balancing act is the strategic process of getting in and out of the car, but now that I have the routine down: get dogs out, stroller out, baby into the stroller. and make sure I have the keys and lock the car, once we get running the dogs actually do pretty well running alongside. It never fails when I have all 3 at least one person says "Wow you've got your hands full" and I have to smile, this just further adds to the fun that I've mastered getting everyone out of the house for a workout at once. The run may not be the most high quality in terms of speed and with occasional stops but I think the effort to push the stroller and control the dogs makes up for it.