Can't get there from here:
John Dvorak is generally down on GPS devices in cars. If you need a high-tech device to find Third street (look between Second Street and Fourth Street, he suggests) you're in trouble.
That said, Boston—a miserably confusing mess—might be a good place for a GPS, except it would be difficult to update the data often enough to tell you what streets are dug up or which one-way street is going a different way this week.
Of course GPS won't work in the Big Dig tunnels, but what does?
