Yeah I fully disagree with you that updates are the problem. You don't need the almost weekly updates being pushed, you do need almost daily charging. But it sounds like you were able to get charging options installed at your place which is cool. I have multiple co-workers who would like to get an EV but they live in an apartment/condo, some with assigned parking and others without. Some have talked to their mgmt companies and laughed at when they ask about getting charging installed. One said the apartment complex would install "one" it but at the club house and it'd be first come first serve, kinda a win?
I think it depends on the developers and the tenants to push for it, yes it can be done but like you said there is a cost to it for sure. Wifi is pretty much everywhere, easy charging without fighting for a parking spot... not so much in my experience but that's my experience.
I think AT&T would start charging Tesla more on the future contracts if Tesla wanted going to start pushing updates over the air which would increase the price of premium connectivity. $10/mo isn't bad right now but all them 1's and 0's do actually cost money which will be passed on to us users. It's one thing to get data capped 1TB for your home internet but a mobile device, even those have much smaller data caps or very slow speeds when hotspotting (looking at you Verizon) and I'm on a true unlimited plan with Verizon.
