Verizon has really ridiculous pricing for adding on features to a family plan. You start @ $70 for 700 / minutes with 2 phones, then add on text messages @ $10 each for for 1000 or $30 for unlimited on the whole account, then add data packages for each phone that start at $30 for smart phones. So minimum, if you want a smart phone for yourself and text frequently, and no data or text on the second phone, it's $110 + taxes and fees. If you want to get a smart phone right now without signing a new contract the cheapest option is to get something like a Droid X used (around $100), activate it on your existing plan, and then start a new contract when the iphone 5 comes out if that's what you really want.
The other option is pre-paid plans like MetroPCS, Cricket, or Virgin / Boost (both Sprint). I don't know much about Metro or Cricket, but the Sprint based pre-paid plans are not that bad if you can live with using the Sprint network only (roaming is not an option). I think Wal-Mart offers a plan too that is based on the Sprint network but the data is really stingy.
Just really depends on what your needs are. Verizon has the most coverage (but other post-paid plans will roam on Verizon's network), Sprint has the most liberal data plan (if you like streaming media it's the best choice), and AT&T is the best if you like getting bent over with shit coverage and data. T-Mobile is trying to bail on the US market so I wouldn't even consider them! Prepaid is the best if you want to save money and not be stuck in a contract with a ridiculous ETF, and you can live with the coverage restrictions.
Buying a phone is easy right?

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