I would buy a Trophy or some other smartphone off-contract for under $200 (whatever your preference - Android, iOS/iPhone, Blackberry, or even a webOS device), hold onto that for a few months, and then buy a new WP when you renew your contract. You don't have to upgrade to a new WP immediately when it becomes available; that will allow you to spread out your costs. Besides, the longer you wait, the better the WP selection on Verizon will (hopefully) become. I'm guessing your current contract with Verizon still qualifies for the new every two promotion, and it's not like that will go away if you wait a couple extra months to purchase a smartphone.
For whatever it is worth, I bought a new Trophy about a week ago, adding a second line; I really wanted to test out other mobile OS besides Android to see what I want long-term (plus I have an increasingly severe smartphone fetish
). I bought it with the expectation that I probably will NOT go 2 years with it; I'll probably A) discontinue the line at some point due to either finances or buying a newer WP when my contract on my Droid 2 is up in late 2012 (the Droid 2 line is grandfathered in with unlimited data) or B) buy a new WP (or other non-WP smartphone, if a WP replaces the Droid 2 on that contract cycle) at full price to upgrade from the Trophy and be able to upgrade again (on the second line) roughly a year after that when the second line contract expires/is up for renewal.
Buying a smartphone off eBay or some other place at full price, while more costly in the short-term, provides more flexibility in the long-term, particularly in cases when a smartphone goes to meet its manufacturer, by allowing you to switch phones in and out of lines/contracts.
I'm thinking about just buying a cheap phone from Walmart with prepaid minutes. I really don't need a smartphone, since I use the Focus more than the Imagio, anyway. I will, however, keep paying for the Imagio's plan just so I can keep my unlimited data once I get my next phone.
Arg! I just can't decide what to do!
Make sure you break down the monthly costs of buying a cheap phone with prepaid minutes AND maintaining your Imagio data/voice plan vs. buying a smartphone off-contract and having it replace the Imagio. Also, I'd be conservative in my time estimate for how long it will take for there to be another WP on Verizon. Verizon almost definitely will want all future WP devices to have 4G LTE, so it may take a little time for those devices to show up on Verizon. The longer it takes one of the smartphone manufacturers to release a 4G LTE WP device on Verizon, the better the idea of buying a smartphone off-contract and replacing your Imagio with that device in the short term becomes.
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