These are not insurmountable problems, but they are expensive, or very time-consuming ones.
You also can't just run a power cord from a wall outlet to the street. You'll need to tear up the sidewalks, to connect the charging stations to the grid. In many places, power isn't underground, so you'll have to bring it down from the power lines to the underground - maybe through the buildings?
This quickly starts running to far more then $1000/charging station, and closer to $10,000/charging station.
This is what curbside parking looks like where I live:
https://www.google.com/maps/@47.6236671,-122.3252994,3a,73.2...
It would cost a fortune to wire that up. Better yet, if only half the streets in the area were wired up, due to the saturation of parking spaces, it would be close to worthless.
Replying to your edit: If you're installing them for a whole street at once, then the cost of bringing power down from a pole or digging under the sidewalk gets amortized across them all. We already hook every house up for water, gas, electricity, and communications. Providing power to every parking spot doesn't have to be particularly hard. It's not so easy you can ignore it, but nor is it a particularly big deal, not when looking at a timespan of decades.
Yes, you can slowly convert the whole area to support street-level chargers over the next few decades - but until you do, having chargers on ~20% of the streets would be next-to worthless. There is a dire shortage of street level parking in this neighborhood - if you limit your possible spots to the ones where chargers are available, it's quite unlikely that you'll be able to get a space.
There does seem to be a chicken-and-egg problem as you describe. Making the spots with chargers EV-only would mitigate that, although I'm sure it would be unpopular with the non-EV owners. It would help if cities got out of the business of subsidizing parking for their residents, but that ship sailed long ago.
I don't see that happening any time soon, and if it does the huge capital expenditure will have to be passed down to the consumers, reducing the economic attractiveness of electrical.
That may still sound like a lot, but the parking spot itself typically costs $2,000 or so, and you're saving on the cost of the gas pump that this charger helps to replace.
Yes, you have to account for the cost of charging infrastructure when looking at the total cost of an EV, but it doesn't greatly change the picture.
we have heating blocks for cars that park outside in north america. If you can install a street light, it's not that hard to install a curbside charger