First off, let me say that I am not a professional installer. However our neighborhood has asked questions like this before and these are some things we came up with.
Typically you will need HOA provided power and internet (ie not piggybacking off a resident's service) at every location where you want a camera. You will need an equipment box that can house all the required equipment (cable modem, router, switch, etc, etc) and hardwire all cameras into this box. Obviously the box, cameras, and wiring needs to be vandal proof. Even if the system provides for local storage of the videos, you would certainly want the video to be uploaded to an offsite location that is also in HOA control. The good news is that with just one dead-end street, you really only need cameras at the starting end of the street. You will need multiple cameras, but probably only one equipment box.
That being said, the equipment side is probably the easiest part of this whole issue. Doing this will open pandora's box with the residents and you will have to answer a lot of questions/details. For example, who has access to the camera feeds? Is it just the HOA board, or select residents, or can any resident pull the feeds up? (I will recommend that you never limit access to just one resident. That is just asking for problems). How to your ensure privacy of your residents while still being effective? You have to nail down these details or they may come back to haunt you. Even if all the current residents want the system, imagine what can happen when a home changes ownership and new residents move in.
I'd recommend getting a professional installer involved in this project to ensure it is done properly. There will obviously be a decent upfront cost as well as the ongoing service costs for power and internet. Unless you are in a high crime area, it is probably more hassle than its worth.
I have a CCTV system at my house. But everything this comes up in my neighborhood, I'm against it for all of these reasons and more. Personally I'd rather see residents buy their own Ring Doorbells before I would have the HOA install a system - and I don't like Ring Doorbells.... lol.