I still have an iPad 1. I use the latest version of XCode for app development which will only debug apps on devices that run iOS 6.
Unfortunately, iTunes will not allow you to upgrade an iPad 1 past iOS 5. Can XCode be configured to debug apps on iOS versions older than version 6?
Another approach would be to upgrade the device to iOS 6 via jailbreaking. I have read that jailbreaking an iPad 1 will give you a path to upgrade it to iOS 6, but I haven’t found anything specific to development.
EDIT
It turns out that this problem only occurs when I create a new app using XCode. However if I open sample code from some existing apps (for example SpeakHere), my iPad 1 suddenly appears on the XCode “run list” and I can test on the iPad 1! I suspect that there is something about these apps that is “old” that causes them to work. Can I simulate that somehow on new apps I build using XCode?
It sounds like you’re just accepting the default deployment target of 6.0 for new projects. This means you won’t be able to run the application on older versions of iOS, much less debug them. You need to set the deployment target for your project or target to 4.x.