There will be a solution to each and every problem - one way or another. Can't lay cables on the ground, build overhead stanchions from building wall to edge of curb and then drop the power. We used stanchions a lot in the aircraft business. Or, dig a ditch across the sidewalk. Or hydrobore under the sidewalk if it is a landmark.
Every single one of these problems has a solution.
On July 20, 1969, the US put a man on the Moon and I quit using the word "can't".
We decided to do it and then we went and did it! Pretty simple concept: Decide to do something, apply the resources and get it done.
Gasoline stations will become a dying industry and some enterprising group will convert them to charging stations. Not every car will be totally exhausted any more than we let the gas gauge get down to a smidge higher than 'E'. I like to keep my tank at least 1/2 full - when I had a gas tank. Since I'm retired, I keep the battery totally charged. I've got nothing but time.
All these supposed 'show stopper' problems will look like pebbles before a steam roller when .gov puts up tax incentives, investment credits and other devices to facilitate the construction of charging points. Low interest rates will also help and, yes, .gov needs to bulldoze stumbling blocks. Clear the blocks and turn private industry loose. Make it happen!
It's going to happen in spite of the naysayers. Just remember 1969 and toss "can't" from your vocabulary. I don't want to hear problems, I want to hear solutions.