I agree that playing the waiting game isnt the best choice when it comes to Apple products - I also upgrade my iPhone yearly etc. The 3Gs to the 4 was a good upgrade, due to the number of changes etc. The iPad to the iPad2 isnt a worthwhile upgrade in my opinion, because the updates are rubbish. We have what, 3 or 4 developments?? It was released to keep up with all the other tablets in the market. Apple were forced to release an earlier then planned update because of this, and I believe it ended up with a product which is aimed more for a newer audience - those without an iPad to date - rather then to those who already have an iPad. If you really needed an iPad now I would save some cash and go with the iPad 1 to get you by for the next few months. The iPad 3 will be a bigger update.
Apple are known to bring out the bigger updates every 2 years, or after every 2 cycles. iPhone is a classic example, and now the iPad. The item comes along, then a small update in between, before the next 'big' update comes along. With the iPad, I'd rather wait for the next big update as my current iPad does everything I need it to do perfectly fine. I would have probably done the same with the iPhone this year, as I believe it will not be a huge update - a slightly bigger screen, and a speed boost maybe, more like a iPhone 4s, rather then an iPhone 5 as such - but my contract ends in June so will look for a decent deal if one is available.....