As far as I know the city wont charge you to shut the curb stop off so that you can replace the main valve. You might have to 3-1-1 that one I am not sure.
The nature of leaks like this is that if left undisturbed it could very well hold for years, but as soon as you start cutting out pipes and making repairs more problems and leaks can surface easily.
At the very least you should cut out the fitting that has a leak and replace with new.
I think the kid with hair cut has the right idea.
I wouldnt want to give you a quote telling you what you want to hear that it is a quick fix, and as soon as the plumber starts cutting and moving pipes, more leaks surface, and before you know it, you will blame me and my plumber for trying to fix it the first place.
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