The headline is somewhat off... the initial cost will be $99 but if it comes along with a contract with any North American mobile carrier then there's no doubt they'll make that money back and more.
Similar to the T-Mobile G1, which currently has a cost somewhere between £180 and £720* despite the handset being 'free'.
Nevertheless there are times when finance can be a great deal. Anyone who took out a cellphone contract in Zimbabwe just before the huge deflation must be enjoying their fixed price (now costing ~0.0000000001% in real terms) right now.
*Depending on how you value the cost of the supplied services - the £180 is for someone who fully utilises the bundled minutes/data valued at the lowest cost I can find of obtaining the same plan elsewhere.
that works out to about €600-700. Stand-alone netbooks go for around €350-400 typically, so you'll have to use about €200-350 worth of the data plan over the course of 2 years. Unless this is their only connection to the internet, I very much doubt most people will use it that much.