To pay $500 for a phone, versus the $100 subsidized price, is a silly move—especially if you're planning to upgrade every 2-3 years.
I say this because the service from the carriers still costs the same regardless of how you obtained the handset, and in some cases you may be paying even _more_ for service if you don't have a contract.
(Of course, I'm speaking with the US/Canadian carriers in mind. I know things are better outside of North America.)
T-Mobile's non-contract plans are $20 less per month, so over 2 years you save $480.
I've got a few contract-only perks here in Canada on Rogers, such as the 6GB data plan add-on for $30/mo, and an "Employee Purchase Program" discounted voice service at $17/mo.
I don't think you can get non-contract data plans for under $30, and that only buys you 250MB/month, and voice plans start at around $25-30/month.
I may be able to set up a similarly-priced plan up here, but I would lose out on many of the important features (tethering, visual voice mail, larger data caps, free evening/weekend calling, etc.)
Since the initial N1 model used the Tmobile 3G bands, it made a perfect match, and a great deal for anyone willing to do the math.