Worst case scenario would be that you can't buy an iPad for what you sold it for and lose a bit of money.
I think it stifles innovation when customers are willing to blindly buy a product without seeing what updates it will bring.
Have you noticed that Android phones are evolving faster than the iPhone? Clearly Apple wins in terms of software for a lot of people, but nobody can deny that Android phones in terms of hardware are evolving faster. Android phones have 4G support, NFC, quad core processors (very soon), hd screens, etc.
Android phone manufacturers are lagging behind Apple so they're working hard to try to entice customers, hence the level of evolution seen. However, because of how popular iPhones are, Apple can be complacent and people will still blindly buy the next product. If less people did this, we could be seeing iPhones which are also rapidly adopting the fresh technology that so many people have asked for countless times and been disappointed with when Apple hasn't listened.
Android may have a greater market share than iOS but no single Android device even comes close, hence why Apple can be complacent.
----------
If there's something you don't like about the iPad 2 then fine, upgrading is a no brainer.