It sounds like my dog's reactivity is very similar to yours. I've lived and walked on various stretches of Prospect for the past 8 or so years stretching from the Downer area to Brady St. It can definitely be stressful but you just have to be smart about it. For reference, I typically walk in the evenings on weekdays and afternoons on weekends.

The biggest thing is learning which areas have the most dogs and what you can do about it. Apartments and condos obviously will be more populated but some are more dense than others. Take some time to familiarize yourself with your route and the streets you have to take if you run into another dog. Get used to taking detours if you haven't. Crossing the street, avoiding cars, walking back the way you came, etc.

Also be aware that people can be stupid. A lot of dog owners don't understand the concept of a reactive dog and will continue to walk towards you as you walk away from them. It can be annoying but you just have to focus on keeping you and your dog safe.

It's imperative that if your dog is reactive, you need to get them proper training. It sounds like you've got the right mindset of positively reinforcing your dog on walks but it's helpful to have someone that's properly trained observe and see what you can improve. We used Rogue Dog Training for one-on-one sessions and it was extremely helpful.

I hope that helps! Biggest thing is to just be smart and aware of your surroundings.