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All the trucks you are looking at are fine.
My son drives a 1999 Tacoma, a friend of his just bought a '12 Ranger and another buddy a '12 F-150. All three have been excellent.
I would go with the extended cab (two doors with a small sing door) F-150 like the one Jack's bud has. Your son's are going to grow. When they all go out together they take the F-150 since the other two trucks are smaller and much less comfortable.
Plus, there will be more room for gear.
Not what you wanted to hear, but I have been driving a 1/2 truck as my DD for over 12 years without any issues with parking in DC, maneuverability, etc. I am also 6'4" so the smaller trucks are not nearly as comfortable for me.
I have never thought. "I need a smaller truck..."
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1996 FJ80.
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