Norway has had the highest sales numbers for EVs in the world, and for the last year or so it has been at over 50 % of all cars sold. Our incentives against fossil fuelled cars are massive, and ever increasing. Still, only 13 % of our total cars are EVs. Sure, the distribution is not equal, so you can get some complexes with a lot of EVs. But then you can splurge for the advanced chargers and systems there. There is no need to borrow problems and install super complex stuff that will get outdated before the fossil cars have been replaced. In fact, it might be a good idea to take this step by step, since the "smart" chargers usually can use the same wires as the "dumb" ones. I do agree that when you get a large number of EVs in one spot, load management is a thing. But that can be solved much easier than connecting it to payment solutions and paying admin fees to someone else. The simplest solution is to allow a max load for all the chargers. If you are alone, you get all the juice. If there is one other car it is split in two, and if everyone is plugged in, it will be down to trickle charging for everyone. There are also solutions available for giving variable load depending on the time of day. K.I.S.S.
No, most people don't charge every day. Even most of those who have cars with small batteries don't charge every day.