Yeah, corp discounts help (24% for me) and the family talk plans are actually pretty reasonably IMO, but where they get you is the data lines. They add up, and my discount doesn't apply to the rest of the family's data. Ultimately, I'd like to see VZW provide a cheaper data option for smartphones, like 2GB for $20, 5GB for $30, etc. Or roll the extra line charge into the data line charge. $20 per month for an extra line with a smartphone wouldn't be bad at all. $30 starts to sting. $40, which is where we are now when you combine the data package with the extra line charge, really starts to hurt, IMO. Otherwise I think they're going to see a cap in the market in the not too distant future where the geeks are saturated and everyone else is fine with a feature phone.
(Remember when you only had to charge your phone on the weekend? And VZ Navigator was enough to get you around? And your bill was half as large? I miss those days sometimes... I really do. If we had to pay full price for our smartphones, would we all make the same choices? I'm not sure I would. There's a really distorted market out there feeding on this cycle of subsidized phones and high data charges...)
So I guess my reply for the OP is, it's a choice. You know where that $50 a month, or whatever it would take to get you from a regular cell phone to a smartphone, is going in your household. If the $ are more useful to you paying rent, or putting food on the table, it's a no-brainer- A smartphone is a fun toy, but a regular phone is fine. If the $ are more useful to you playing WoW, then it's a choice you've made with your discretionary $$, plain and simple. I could ask the same question of people with IPads, or any tablets with an additional data plan - I don't see how people afford them. I don't choose to spend that much money on my electronic toys, so by definition it's tougher for me to understand the perspective of someone who does.
On the other hand, I do choose to spend discretionary $$ on firearms, ammo, diving gear, a motorcycle, etc. So when I see a techno-dude e-mailing from his iPad and feel that little twang of, "Man, how does he swing that," I stop and remember that almost everything we do and have really comes down to the choices we have made for ourselves.