Aw man. As a bootstrapping web business guy, I can say I've had way more problems with supporting iPads and iPhones than IE. IE costs me $0 to support, and I don't even bother (nobody asks!). Supporting hip and popular Apple browsers can run me a grand in a fast minute. Pleasing early adopters without working really well on the iPad3 is a tough sell. I think startups fighting to support I'm not crazy about getting an…
I'm confused why you believe you need hardware for testing? iOS simulator should be plenty sufficient in any standard dev environment...
My larger point is that the hassle isn't supporting X version of a browser anymore, it's supporting X version of a browser on various hardware devices. Web-dev hell isn't going to be the fault of IE anymore, it's going to be the fault of mobile platforms with differing browsers, screen-sizes, and use patterns.