should/would

I see people advertise their cars for sale in by the streets. So I thought I should/would give it a shot.

Either works for me.

I should give it a shot = I ought to try it

I would give it a shot = I will try it.

In? Where's the car located with in? [in/on] the streets is really difficult to understand despite the fact that I've tried to analyze it numerous times.

How about 'on the streets"?

I presume that you mean the cars are advertised by a sticker in the car window.

I'm not aware of a specific term for this form of selling a car, but I suppose they are advertising their cars in/on the street where the car is located. I would accept either in or on.

I park in/on the street.

This reminds me of the discussion in/on the drive. Despite the posts I would us

Another street question, A car is speeding in/on the street?

A car is speeding in/on the street?

I would accept either. Others may not.

Thanks, Optilang.

In my experience, the British are far more likely to accept in in those cases than Americans, who prefer on (but may accept in as well).
CJ

One day, I'll compile all possible scenarios about streets and figure it out once and for all. It's still very confusing. My chance of getting it right is 50 50.

I would say:
I see people advertise thieir cars for sale on the street(s), so I thought I [would / should] give it a shot.
would means you are inclined to "give it a shot" because you want to. You've almost decided to go ahead with the plan. Or perhaps you have already decided to go through with it.

should means you are inclined to "give it a shot" because you fee

New2grammarMy chance of getting it right is 50 50.

I wonder if that doesn't actually mean 100%, because there's always someone who will believe it's correct, no matter what your choice.