We didn't get updates all the time back then because we didn't live in a "beta" world. However items, even electronic ones, were more basic back then. And nowadays, if you can't deliver a product quickly, even if it isn't 100% ready, then you're already way behind the competition. Regardless of what a contract says, it is pretty much implied that constant evolution of a product is guaranteed, particularly for a higher end product.
Could you imagine that the PS3 would still be selling if it was the exact same product it was when it first released or if they only provided new firmware only if you bought a new PS3?
You make a good point about marketplace expectations. But I think you're comparing apples and oranges to some extent. Once a customer purchases a PS3, most additional profit doesn't come from selling him/her another gaming system. It comes from selling new games. Thus, a manufacturer has a strong incentive to maintain an up-to-date device for the entire installed base.
On the other hand, carriers (at least in this country) derive most of their profits from long-term contracts. If a customer opts to jump ship part way through their contract, the various fees allow the carrier to recoup their subsidy AND potentially to sell you a new device with a new two year commitment.
If Verizon charged you for updates or apps they'd be in the same position as Nintendo, Sony, or Microsoft with their gaming systems. But they don't. And if you had to extend your contract with VZW to get the 2.2 update, they'd rush it out as soon as possible. But again, that's not part of the deal.
Of course, VZW may make you an unhappy customer by not providing updates on a prompt schedule. But unless you're so unhappy that you leave for another carrier, it's not a problem for their bottom line. And even if you leave, if Verizon can find someone to replace you with a new snazzy phone model with a two year contract commitment, they don't suffer, either.