Rips, what are you defining as a "road" here? walking a dog off lead along a dead-end country road and walking a dog along a 50mph road with constant traffic are obviously a bit different. It is all good and well saying people don't know you, your dogs, your area, etc., but unless you actually clarify what you mean...yes people are going to make judgments/generalizations about what you are saying!

Is it Oscar who is nervous of people or other dogs? I think I remember you posting about him being 'freaky' or reactive (apologies if this is not you)...how does this come into play if you are walking him off lead by traffic?

This is one of my biggest pet hates!
Around here it's mainly staffies who are being walked like this, and a LOT without a collar or harness even! So no tag or anything to hold onto if they bolt.
A lot of the others are walked with a collar but no lead on...even though the owner is holding the lead in their hands! How hard is it to then attach it to the dog?!
I always get an urge when in the car to yell out to the people to put their dogs on a lead, but I don't incase it scares the dog into running into a road.
I don't differentiate between them 'showing off' or just 'trusting' their dogs...it's equally senseless to me and I can't agree with such practice.

Er I did shout at someone once when I was in my car and their dog was near the road. It really shook me up as I was scared it was going to run into the road in front of me!