you definitely can 'meter' the demand to some extent with automation, all it would require is for you to put in your next planned trip departure time (needs to be charged by) and hook up to the internet, your electric provider can monitor overall usage and provide capacity information in real time which your charge controller uses to avoid overloading the grid(the current grid still isnt up to the task of charging that many vehicles IMO). Definitely a doable thing in the future(hell doable now if the code were written most likely), but its not all in place yet and as you mention it will take time to get there, i agree most like 20 years or so before we see a major uptick in that dept (i could be wrong, but current tech, especially in the battery department doesnt seem to be evolving fast enough to accelerate that, for now).
Tesla quotes 8.5-12hr for a full charge, that means if you have two commuters in the house and you get home between 5 and 6 at night (pretty standard i think) and you leave between 6 and 7 (again i think this is pretty average, at least seems to be for people i know) that is 12 hours, you cannot fully charge both cars without overlapping SOME of the charge time, and even if you only need a 50% charge each night (just a number) thats still 6 hours, your adding that much draw at each house for the entire period that you are home overnight. Will battery and charging tech improve so that you can charge up faster and hold more charge?? certainly, but we arent at a point yet where its possible.
eventually there will be a time where all cars are electric, parking meters will feature a charging cable and cars will be chipped and linked to your CC (similar to ezpass) so when you park you plug in, they charge your account for the energy you add to your battery, and for any parking fees associated with it (could even be as simple as an NFC chip to do this part, so there is no cheating on paying for your parking by only charging if needed). but again, thats a MASSIVE infrastructure change and will not happen quicly.