Maybe I have a different perspective because I bought my iPad 1 a few months after the two came out, knowing I was buying yesterday's tech. But, it is still in brand new condition, under Apple care, and running 5.1.1 like some of you.
I understand that this is the new world of disposable electronics, with 2 year life cycles vs 3-5 years.
My suspicion is this... soon, there will be no more support for 5.1.1, and iPad 1 users will have a choice 1) jailbreak and rely on 3rd party support, which is a very simple (for non techies) and very viable solution, or upgrade. I hope to get another year, or so, out of my ipad.
Whatever any of you choose to do, it's important to understand that this is not personal, and it's not money grubbing. It's business and it's progress. The annual ipad release isn't geared towards existing ipad users, it is for whomever hasn't bought one yet. We are just a bonus. But, we have to understand that they can't support us forever. If we don't want to upgrade, we need to support ourselves, and live with the limitations of our devices.