Regardless of how old your plan is, you can upgrade to a new iPhone 3GS for $200 more than then 2 year plan price... meaning $399 for a 16GB and $499 for a 32GB. This is an "early upgrade" option, which resets the clock on your 2 year contract.
I'm probably going this route since I bought my 3G about 4 months ago, and can probably get 400-450 for it since it's 16GB. Once QuickPwn and ultrasn0w are released, my phone will go on the market as a 16GB 3G running 3.0 jailbroken and unlocked. Should definitely sell fast.
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