The grid is the bottleneck, installing 100s of charging stations is quick and easy, getting them operational on the grid is a BIG problem.

My understanding (and I could be completely wrong, I didn’t investigate) is that the curbside chargers I saw in Boston were Level 1, that is 110v. You could get 30-40 miles of charge overnight, certainly enough to get you to a commercial fast charger if you needed to. And even if you put 1,000 of them in, as they were located in “night street parking” only, it would have virtually no effect on the grid, using only base power at times when the grid is already under-utilized (having been built for peak times in the morning and late afternoon.)

As for deploying it, I’m pretty sure National Grid or whoever is constantly maintaining their underground lines; I know in Chicago’s Loop there were actual tunnels you could walk (hunched over, but still…) through which carried electric, telephone, fiber, and coax delivery throughout the area. While I doubt Boston has anything similar, they also don’t have overhead wires and they somehow managed to get cable TV installed everywhere when that industry came along.

There will be different situations and different solutions I am quite sure, but solutions there will be.