A good chunk of this is caused by our city repeatedly choosing awful vendors that bilk the city for crazy amounts of money, and provide trash as the final product.
City Light and the new meters/new billing system are great examples, all the new power meters have no encryption, and use FSK for modulation. Asking City Light about this got me a response that FSK was the encryption, and the gal was dumbfounded when I pointed her to the Wikipedia article on FSK.
On the billing side, an Oracle salesman ran off with over $100 million in city funds for what is essentially a CRUD app, and the worst part is they didn't bother to customize this system, just forklifting this in place and letting the chips fall where they may. The prior billing system had quite a bit of data validation and business logic that has yet to be implemented or replicated on this new system. The same actions when you call customer service now take significantly longer.
Both these vendors fleeced the city for broken, insecure systems, and neither is having to face the music for it. Worst part is, eventually someone may attempt a fairly trivial exploit of either system, which could wreak havoc in our city.