Why would it require that? In the UK instead of doing all that the councils have been installing EV charging points into streetlights, negating any requirement to dig up the pavements (beyond that required to replace a streetlight) to install these.

Philadelphia is an interesting choice of example. I've seen charging cords going out windows to cars from time to time, facilitated by the popularity of the rowhouse. (IMHO even in south philly, you can usually snag a spot in front of your house several times per week if you care enough to try-- if you only drive enough to charge once or twice a week this is already enough)

Obviously not an ideal solution but a good example of the kind of stop gaps we'll be seeing over time.

I'm also already seeing rapid chargers frequently in strip malls and stuff. So maybe doing errands and spending at least an hour there once a week will be another stop gap.

Considering how often streets get repaved and that we're talking about gradual change over the next decade or two, and that there are inferior but workable stopgaps as mentioned above (that will allow people to get by, yet also incentivize them to loudly demand better) I think there's time to add the charging stations necessary as needed without any serious issues.

I've been thinking about this for a bit (I happen to live in Philly) & I think the easier answer for cities is instead of focusing on charging "at home" parked on the street, to instead go all-in on destination charging (charging at work, at the grocery store, etc).

Adding charging to a garage or parking lot is easier than on the street, and you don't have to worry about not being able to access "your" spot.