Hey Skott! I have a Pug crossed with a Pitbull or Boston so he's about the same size or smaller than yours. He was not down with running with me either to begin with. My advice is to start running your dog in the spring and try it out. It took about 4 months of 15 to 20 min runs with my dog Doug to train him to run with me but he is a trooper now and we did a 10 km run together last Sept.
I never thought he would be a good running partner but I got him a harness instead of using his collar when we run and I tell him to mush lol. He gets excited in the snow and pulls me along. He's always there for me in the morning although he needs a pep talk sometimes.
It's worth trying - good for you and your dog. And your smiling experiment will work after time. Maybe you'll see the same people on your route and be able to say hello. After I started running in my neighborhood, I started to notice the people I saw everyday would smile back and now I wave to them in the morning and it's become part of my routine.
Hey Skott! I admire you for trying so hard. Can you get a training buddy to go with you? This may sound strange but if you can't find a person, find a dog. I didn't like running. I still don't like it, but if my dog is with me, he makes me smile. I might have to stop a few times for him to do his business but the overall benefit I get from the company is well worth it. I may not run as fast or as long. But it makes me happy. And he is stoked to come with me, rain, snow or shine :). He is by far the best training buddy I have ever had.
I find audio books a nice change from music and you can really focus on them. Inspirational self help tapes easy to find free on VUSE. Happy running! Have to tried the toes socks helps keep the toes cool and toe socks with grips for yoga :) I love them!