Kenny, I'm sorry about your loss, but don't blame yourself. Like others, I lost 3 dogs and a cat as well. Tho all the 3 dogs were put to sleep, the last dog died in terror and pain in my arms. I still have trouble with myself for being "angry" at her when I knew she was just to old to "hold up", what she needed to do outside. That was one of the reasons my family decided to put her down. (I wanted her to die in a natural way).
Please, explain to me how to raise an animal with street smarts
I don't think you can do that. Not 100%. Few things you can teach a dog.
Ignore other dogs / cats (on the other side of the road)
Make him / her sit at every road even i there's no traffic. Don't let him / her cross untill you tell him to.
Keep in mind that I don't think it works if the dog is having fun running around. IE, it wont't stop and wait for the command to cross a road.